CN114276203B - Method for synthesizing 2-aminobenzamide compound by ultraviolet light induction - Google Patents
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Abstract
The invention develops a method for synthesizing 2-aminobenzamide compounds by ultraviolet light induction. The method takes 2-nitrobenzaldehydes compounds and primary amine as raw materials, and can obtain the 2-aminobenzamide compounds by carrying out dehydrogenation N-acylation reaction and nitro reduction reaction under the irradiation of ultraviolet light in a room temperature environment. The method has the advantages of wide substrate range, mild reaction conditions, high yield of target products, simple and convenient reaction operation, small reaction pollution and the like, and has certain feasibility for industrial large-scale production.
Description
Technical Field
The invention relates to a synthesis method of a 2-aminobenzamide compound, in particular to a method for synthesizing a 2-aminobenzamide compound by using an ultraviolet light-induced 2-nitrobenzaldehyde compound and primary amine, belonging to the field of organic chemistry and chemical industry.
Background
2-aminobenzamide compounds are an important class of organic synthesis reaction intermediates, which are often used for preparing some complex nitrogen-containing compounds. For example, the synthesis of quinazolinone compounds typified by hypnone, mecloquine, luponin F, boucharin, and sildenafil requires the use of 2-aminobenzamide compounds as synthesis precursors. In addition, the synthesis of 4-imine-4H-3, 1-benzoxazines and N-substituted 1,2, 3-benzotriazin-4-ones also requires the use of 2-aminobenzamides as reaction intermediates. 2-aminobenzamide compounds can also be applied in medical research because of certain biological activities of the framework structure of the compounds, such as antibacterial activity, antithrombotic activity, glycogen phosphorylase inhibitory activity and Thyroid Stimulating Hormone Receptor (TSHR) antagonistic activity.
The synthesis method of the 2-aminobenzamide compound which is reported at present comprises the following steps: the method comprises the following steps of ring-opening reaction of isatoic anhydride, amination reaction of anthranilic acid, N-arylation reaction between 2-bromobenzylamine and benzonitrile, amidation reaction of 2-aminobenzonitrile and alcohol, N-Fries rearrangement reaction of N-carbamyl diarylamine, ortho-position selectivity C-H carbonylation reaction of palladium-catalyzed N-substituted aniline and the like. However, these methods for synthesizing 2-aminobenzamide compounds have high requirements on the water oxygen content during the reaction process, are not easy to operate on a large scale, and have the problem of heavy metal pollution in the post-treatment of part of the reaction. Therefore, it is important to develop a simple and green method for synthesizing 2-aminobenzamide compounds.
Disclosure of Invention
Aiming at the defects of the existing synthesis method, a method for synthesizing 2-aminobenzamide compounds by ultraviolet light induction is developed. The method takes 2-nitrobenzaldehydes compounds and primary amine as raw materials, and can realize the synthesis of the 2-aminobenzamides compounds by ultraviolet irradiation at room temperature.
In order to achieve the above object, the present invention provides the following technical solutions:
the method comprises the step of carrying out dehydrogenation N-acylation reaction and nitro reduction reaction on a 2-nitrobenzaldehyde compound I and primary amine II by using a mixed solution of ethyl acetate and acetone as a solvent under the condition of acetic acid through ultraviolet irradiation at room temperature to obtain a 2-aminobenzamide compound III.
As a preferred scheme, the 2-nitrobenzaldehydes I have a structure shown in a formula 1:
wherein Ar is various substituted phenyl groups and various substituted pyridine ring groups. Ar in the 2-nitrobenzaldehydes of the present invention may be various substituted phenyl groups including mono-substituted phenyl groups and poly-substituted phenyl groups, and the position of the substituent is not limited, for example, phenyl group substituted with chlorine atom, methyl group, methoxy group, etc. at the 4-position, and also, for example, phenyl group disubstituted with methoxy group, etc. at the 4-position and the 5-position, etc. Ar can be various substituted pyridine ring groups, and also comprises mono-substituted phenyl and multi-substituted pyridine ring groups, and the position of the substituent is not limited.
As a preferred embodiment, the primary amine II has a structure represented by formula 2:
R-NH 2
formula 2
Wherein R is C 3 ～C 12 Aliphatic hydrocarbon group of (2), C 3 ～C 6 The compound is a compound of the following formula (I), wherein the compound is a cycloalkyl, various substituted phenyl, various substituted benzyl, various substituted heterocyclic groups and various amino acid ester groups. In the primary amines of the invention R may be a saturated aliphatic hydrocarbon radical, such as C 3 ～C 12 The saturated aliphatic hydrocarbon group of (A) is C 3 ～C 12 The alkyl chain may be a straight chain, a branched chain, or a substituted group, and specifically includes isopropyl group, n-butyl group, 3-isopropoxypropyl group, dodecyl group, and the like. R may be C 3 ～C 6 The cycloalkyl group may have a substituent, and the position of the substituent is not limited. R can be various substituted phenyl groups and various substituentsSubstituted benzyl, various substituted heterocyclic groups, various amino acid ester groups, and the types of the substituent groups and the positions of the substituent groups are not limited.
In a preferred embodiment, the 2-aminobenzamide compound III has a structure represented by formula 3:
wherein Ar is various substituted phenyl groups and various substituted pyridine ring groups; r is C 3 ～C 12 Aliphatic hydrocarbon group of (C) 3 ～C 6 The compound is a compound of the following formula (I), wherein the compound is a cycloalkyl, various substituted phenyl, various substituted benzyl, various substituted heterocyclic groups and various amino acid ester groups.
In a preferred embodiment, the molar amount of the primary amine is 2 to 4 times the molar amount of the 2-nitrobenzaldehyde compound. The yield of the target product is obviously improved when the proportion of the primary amine is increased, and the yield of the target product is not obviously improved when the proportion of the primary amine exceeds 4 times that of the 2-nitrobenzaldehyde compound.
In a preferred embodiment, the molar amount of acetic acid is 0.5 to 2 times the molar amount of the 2-nitrobenzaldehydes. After the acetic acid is added, the yield of the target product is obviously improved, and when the addition amount of the acetic acid reaches 2 times of that of the 2-nitrobenzaldehyde compound, the yield of the target product of the reaction reaches good.
As a preferred scheme, the solvent adopted in the reaction is a mixed solvent of ethyl acetate and acetone, the ratio of the mixed solvent to the ethyl acetate/acetone is 4. The yield of the target product is obviously influenced by changing the ratio of the ethyl acetate to the acetone in the mixed solvent, and the target product can hardly be obtained when the acetone is not added into the reaction solvent.
The invention relates to a specific reaction principle which may exist in dehydrogenation N-acylation reaction and nitro reduction reaction between 2-nitrobenzaldehydes and primary amine: the 2-nitrobenzaldehydes rearrange to 2-nitrosobenzoic acid after absorption of ultraviolet light and are attacked by primary amines in the acidic reaction environment created by acetic acid. The carboxyl group of the 2-nitrosobenzoic acid reacts with the primary amine to form an amide. The nitroso of the 2-nitrosobenzoic acid is firstly added with primary amine through nucleophilic addition, and then the imine intermediate is eliminated to obtain the hydroxylamine. Under this system, the hydroxylamine group is reduced to an amino group, thereby obtaining the target compound.
Compared with the prior art, the technical scheme of the invention has the following advantages:
first, the process does not require transition metals, bases, and additives;
secondly, the method only needs one-step reaction, the yield is up to 92 percent, and the method has tolerance to various functional groups;
thirdly, the method is simple, mild and green and can effectively synthesize the 2-aminobenzamide compound;
fourthly, the amino acid derivative can be smoothly converted into the 2-aminobenzamide compound at room temperature;
fifth, the method has certain feasibility for industrial mass production.
Drawings
FIG. 1 is a method for synthesizing 2-aminobenzamide compounds by ultraviolet light induction; FIG. 2 is a NMR spectrum of 2-amino-N-benzylbenzamide; FIG. 3 is a NMR carbon spectrum of 2-amino-N-benzylbenzamide.
Detailed Description
The present invention will be described in detail with reference to the following embodiments in order to make the above features, advantages and objects of the invention more comprehensible. In the above description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. This invention may, however, be embodied in many different forms than those specifically described herein, and it will be apparent to those skilled in the art that many more modifications are possible without departing from the spirit and scope of the invention.
The reaction materials and catalysts mentioned in the following examples are commercially available reagents which are conventional in the market unless otherwise specified.
Condition optimization experiment: taking the synthesis of 2-amino-N-benzyl benzamide from 2-nitrobenzaldehyde and benzylamine as an example for explanation, the optimal reaction conditions are obtained by optimizing conditions such as reactant proportion, solvent selection, acid/alkali selection and dosage, reaction time, light source and the like and monitoring reaction yield through a gas chromatograph, and the specific reaction under the optimal reaction conditions is as follows:
adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of benzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by using ultraviolet light with the power of 24W and the wavelength of 365-375nm at room temperature for reacting for 16h. After the reaction is finished, performing column chromatography separation by using a solvent prepared from petroleum ether and ethyl acetate to obtain a target product 2-amino-N-benzyl benzamide, and obtaining a brown solid with the yield of 79%.
As can be seen from the experimental groups 1 to 4 in the above table, the yield of the target product of the reaction increases with the increase of the proportion of benzylamine, and the yield of the target product of the reaction is better when the proportion of benzylamine is 4 times that of 2-nitrobenzaldehyde.
It can be seen from the above tables that acetone is essential for the reaction in the experimental groups 1 and 4 to 9. Meanwhile, a solvent in which the mixing ratio of ethyl acetate to acetone is 6.
As can be seen from the above tables, experimental groups 1 and 10 to 17, acetic acid positively accelerates the reaction, and the yield of the objective product increases with the increase of the amount of acetic acid added, and when 0.4mmol of acetic acid is added, the yield of the objective product is better. While oxalic acid and fumaric acid do not similarly promote the reaction as acetic acid does, the reaction cannot be carried out under alkaline conditions.
As can be seen from the experimental groups 1 and 18 to 24 in the above table, the reaction time affects the yield of the target product of the reaction, and as the reaction time increases, the yield of the target product also increases, and when the reaction time reaches 16 hours, the yield of the target product of the reaction is better.
As can be seen from the experimental groups 1 and 24-28 in the above table, the reaction does not occur in the absence of light, and the yield of the reaction is significantly affected with the change of the wavelength of light, and the yield of the target product of the reaction is better when the wavelength of light is 365-375 nm.
The invention is further illustrated below with reference to specific preparation examples 1 to 32:
preparation example 1
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of benzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of solution of which the mixing ratio of ethyl acetate to acetone is 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N-benzylbenzamide was obtained by column chromatography in 79% yield as a brown solid.
1 H NMR(400MHz,CDCl 3 )δ7.39–7.15(m,7H),6.71–6.58(m,2H),6.35(s,1H),5.56(s,2H),4.60(d,J＝5.6Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.1,148.8,138.2,132.4,128.8,127.8,127.5,127.1,117.3,116.6,115.8,43.7.
Preparation example 2
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 2-methylbenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone with the mixing ratio of 6 as a solvent, and irradiating the mixture by 365-375nm ultraviolet light at room temperature for reacting for 16h. Column chromatography separation gave 2-amino-N- (2-methylbenzyl) benzamide as a light brown solid in 70% yield.
1 H NMR(400MHz,CDCl 3 )δ7.29–7.24(m,2H),7.22–6.99(m,4H),6.68–6.53(m,2H),6.27(s,1H),5.51(s,1H),4.54(d,J＝5.4Hz,2H),2.34(s,3H).
13 C NMR(101MHz,CDCl 3 )δ168.6,148.7,136.4,135.8,132.2,130.5,128.3,127.7,127.1,126.1,117.2,116.4,114.9,41.8,18.9.
Preparation example 3
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 3-methylbenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- (3-methylbenzyl) benzamide is obtained by column chromatography separation, and a brown solid is obtained with the yield of 68%.
1 H NMR(400MHz,CDCl 3 )δ7.30(d,J＝7.9Hz,1H),7.24–7.05(m,5H),6.67–6.55(m,2H),6.47(s,1H),5.53(s,2H),4.51(d,J＝5.7Hz,2H),2.32(s,3H).
13 C NMR(101MHz,CDCl 3 )δ169.1,148.7,138.3,138.2,132.2,128.5,128.4,128.1,127.1,124.7,117.2,116.4,115.7,43.5,21.3.
Preparation example 4
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 4-methylbenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- (4-methylbenzyl) benzamide was obtained by column chromatography in 69% yield as a brown solid.
1 H NMR(400MHz,CDCl 3 )δ7.29(dd,J＝7.9,1.5Hz,1H),7.25–7.18(m,2H),7.18–7.11(m,3H),6.68–6.55(m,2H),6.40(s,1H),5.52(s,2H),4.51(d,J＝5.6Hz,2H),2.33(s,3H).
13 C NMR(101MHz,CDCl 3 )δ169.1,149.2,137.1,135.2,132.2,129.3,127.7,127.1,117.2,116.4,115.8,43.4,21.0.
Preparation example 5
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 4-methoxybenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- (4-methoxybenzyl) benzamide is obtained by column chromatography separation, and a light yellow solid is obtained with the yield of 61%.
1 H NMR(400MHz,CDCl 3 )δ7.32–7.12(m,4H),6.86(d,J＝8.1Hz,2H),6.69–6.55(m,2H),6.38(s,1H),5.53(s,2H),4.49(d,J＝5.5Hz,2H),3.78(s,3H).
13 C NMR(101MHz,CDCl 3 )δ169.0,159.0,148.7,132.2,130.3,129.1,127.1,117.2,116.5,115.8,114.1,55.2,43.1.
Preparation example 6
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 4-tert-butylbenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of which the mixing ratio of ethyl acetate to acetone is 6 as a solvent, and irradiating for 16h at room temperature through 365-375nm ultraviolet light. The 2-amino-N- (4- (tert-butyl) benzyl) benzamide is obtained by column chromatography separation, and a yellow solid is obtained with the yield of 89%.
1 H NMR(400MHz,CDCl 3 )δ7.42–7.33(m,2H),7.33–7.22(m,3H),7.18(ddd,J＝8.5,7.2,1.5Hz,1H),6.69–6.57(m,2H),6.37(s,1H),5.54(s,2H),4.55(d,J＝5.5Hz,2H),1.31(s,9H).
13 C NMR(101MHz,CDCl 3 )δ169.1,150.5,148.8,135.1,132.3,127.6,127.1,125.6,117.3,116.5,115.8,43.4,34.5,31.3.
Preparation example 7
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 4-fluorobenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- (4-fluorobenzyl) benzamide is obtained by column chromatography separation, and a light yellow solid is obtained with the yield of 70%.
1 H NMR(400MHz,CDCl 3 )δ7.34–7.25(m,3H),7.24–7.15(m,1H),7.01(t,J＝8.7Hz,2H),6.70–6.57(m,2H),6.44(s,1H),5.53(s,2H),4.53(d,J＝5.8Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.2,163.3,160.9,148.8,134.1,134.1,132.4,129.4,129.3,127.1,117.3,116.6,115.6,115.6,115.4,42.9.
Preparation example 8
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 4-chlorobenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- (4-chlorobenzyl) benzamide is obtained by column chromatography separation, and a white solid is obtained with the yield of 84 percent.
1 H NMR(400MHz,CDCl 3 )δ7.34–7.16(m,6H),6.71–6.58(m,2H),6.45(s,1H),5.53(s,2H),4.54(d,J＝5.8Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.2,148.9,136.9,133.2,132.5,129.0,128.8,127.0,117.5,116.6,115.5,42.9.
Preparation example 9
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 4-bromobenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- (4-bromobenzyl) benzamide is obtained by column chromatography separation, and a light yellow solid is obtained with the yield of 77 percent.
1 H NMR(400MHz,CDCl 3 )δ7.46–7.43(m,2H),7.31(dd,J＝7.9,1.5Hz,1H),7.28–7.00(m,3H),6.71–6.57(m,2H),6.45(s,1H),5.53(s,2H),4.52(d,J＝5.8Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.2,148.9,137.4,132.5,131.8,129.3,127.0,121.3,117.4,116.6,115.4,42.9.
Preparation example 10
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 4-iodobenzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- (4-iodobenzyl) benzamide is obtained by column chromatography separation, and a light yellow solid is obtained with the yield of 92%.
1 H NMR(400MHz,CDCl 3 )δ7.66(d,J＝8.3Hz,2H),7.31(dd,J＝7.9,1.5Hz,1H),7.20(ddd,J＝8.5,7.2,1.5Hz,1H),7.08(d,J＝8.3Hz,2H),6.71–6.58(m,2H),6.40(s,1H),5.53(s,2H),4.52(d,J＝5.8Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.2,148.9,138.1,137.8,132.5,129.6,127.0,117.4,116.6,115.4,92.8,43.1.
Preparation example 11
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 1-naphthylmethylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of which the mixing ratio of ethyl acetate to acetone is 6 as a solvent, irradiating by 365-375nm ultraviolet light at room temperature, and reacting for 16h. Column chromatography separation gave 2-amino-N- (naphthalen-1-ylmethyl) benzamide as a pale yellow solid in 77% yield.
1 H NMR(400MHz,DMSO-d 6 )δ8.81(t,J＝5.8Hz,1H),8.21(d,J＝8.1Hz,1H),7.99–7.92(m,1H),7.84(dd,J＝6.4,3.3Hz,1H),7.61–7.43(m,5H),7.15(t,J＝7.7Hz,1H),6.72(d,J＝8.2Hz,1H),6.52(t,J＝7.5Hz,1H),6.45(s,2H),4.91(d,J＝5.7Hz,2H).
13 C NMR(101MHz,DMSO-d 6 )δ168.8,149.8,134.9,133.3,131.7,130.9,128.5,128.1,127.3,126.1,125.7,125.4,125.1,123.4,116.4,114.5,114.4,40.3.Preparation example 12
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 2-aminomethyl pyridine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. Column chromatography separation gave 2-amino-N- (pyridin-2-ylmethyl) benzamide as a brown solid in 23% yield.
1 H NMR(400MHz,CDCl 3 )δ8.58–8.53(m,1H),7.67(tt,J＝7.8,1.5Hz,1H),7.48(d,J＝7.9Hz,2H),7.31(d,J＝7.8Hz,1H),7.25–7.17(m,2H),6.67(t,J＝7.8Hz,2H),4.72(d,J＝4.9Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.3,156.4,149.0,148.8,136.7,132.3,127.5,122.3,122.0,117.2,116.6,115.8,44.4.
Preparation example 13
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 2-furanmethanamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of which the mixing ratio of ethyl acetate to acetone is 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. Column chromatography separation gave 2-amino-N- (furan-2-ylmethyl) benzamide as a light brown solid in 61% yield.
1 H NMR(400MHz,CDCl 3 )δ7.55–6.98(m,3H),6.70–6.58(m,2H),6.39(s,1H),6.30(dd,J＝21.1,3.0Hz,2H),5.52(s,2H),4.58(d,J＝5.4Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.0,151.3,148.8,142.2,132.4,127.2,117.3,116.5,115.5,110.5,107.5,36.6.
Preparation example 14
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of tryptamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. Column chromatography separation gave N- (2- (1H-indol-3-yl) ethyl) -2-aminobenzamide as a white solid in 85% yield.
1 H NMR(400MHz,DMSO-d 6 )δ10.80(s,1H),8.36–8.30(m,1H),7.60(d,J＝7.8Hz,1H),7.47(d,J＝7.9Hz,1H),7.35(d,J＝8.0Hz,1H),7.18(d,J＝2.3Hz,1H),7.10(dt,J＝20.9,7.7Hz,2H),6.99(t,J＝7.4Hz,1H),6.70(d,J＝8.2Hz,1H),6.50(t,J＝7.5Hz,1H),6.41(s,2H),3.51(q,J＝6.8Hz,2H),2.95(t,J＝7.5Hz,2H).
13 C NMR(101MHz,DMSO-d 6 )δ168.8,149.6,136.2,131.5,128.0,127.3,122.5,120.9,118.3,118.2,116.3,115.0,114.5,112.0,111.3,25.2.
Preparation example 15
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of aniline and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N-phenylbenzamide is obtained by column chromatography separation, and a light yellow solid is obtained with the yield of 25%.
1 H NMR(400MHz,CDCl 3 )δ7.79(s,1H),7.55(d,J＝8.0Hz,2H),7.49–7.42(m,1H),7.35(t,J＝7.8Hz,2H),7.24(td,J＝7.5,7.0,2.6Hz,1H),7.13(t,J＝7.4Hz,1H),6.73–6.65(m,2H),5.47(s,2H).
13 C NMR(101MHz,CDCl 3 )δ167.5,148.9,137.8,132.7,129.0,127.2,124.5,120.5,117.5,116.8,116.2.
Preparation example 16
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of n-butylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, irradiating by 365-375nm ultraviolet light at room temperature, and reacting for 16h. Column chromatography separation gave 2-amino-N-butylbenzamide as a light brown solid in 76% yield.
1 H NMR(400MHz,CDCl 3 )δ7.29(d,J＝7.8Hz,1H),7.18(t,J＝7.6Hz,1H),6.70–6.59(m,2H),6.09(s,1H),5.48(s,2H),3.40(q,J＝6.6Hz,2H),1.62–1.54(m,2H),1.40(q,J＝7.2Hz,2H),0.96(td,J＝7.3,3.0Hz,3H).
13 C NMR(101MHz,CDCl 3 )δ169.3,148.5,132.0,127.0,117.2,116.5,116.5,39.4,31.7,20.1,13.7.
Preparation example 17
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of dodecyl primary amine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, irradiating by 365-375nm ultraviolet light at room temperature, and reacting for 16h. The 2-amino-N-dodecylbenzamide is obtained by column chromatography separation, and a light brown solid is obtained with the yield of 86%.
1 H NMR(400MHz,CDCl 3 )δ7.32–7.26(m,1H),7.23–7.15(m,1H),6.70–6.60(m,2H),6.03(s,1H),5.48(s,2H),3.40(q,J＝6.7Hz,2H),1.59(p,J＝7.3Hz,2H),1.26(s,18H),0.88(t,J＝6.7Hz,3H).
13 C NMR(101MHz,CDCl 3 )δ169.3,148.6,132.1,127.0,117.3,116.6,116.5,39.7,31.9,29.7,29.6,29.6,29.6,29.5,29.3,27.0,22.7,14.1.
Preparation example 18
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of isopropylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N-isopropylbenzamide is obtained by column chromatography separation, and a white solid is obtained with the yield of 63%.
1 H NMR(400MHz,CDCl 3 )δ7.28(d,J＝7.8Hz,1H),7.18(t,J＝7.7Hz,1H),6.69–6.58(m,2H),5.92(s,1H),5.48(s,2H),4.22(q,J＝6.8Hz,1H),1.23(d,J＝5.9Hz,6H).
13 C NMR(101MHz,CDCl 3 )δ168.5,148.5,132.0,127.0,117.2,116.5,116.5,41.4,22.8.
Preparation example 19
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 3-isopropoxypropylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- (3-isopropoxypropyl) benzamide is obtained by column chromatography separation, and a brown oily liquid is obtained with the yield of 61%.
1 H NMR(400MHz,CDCl 3 )δ7.32(dd,J＝7.9,1.5Hz,1H),7.21–7.13(m,1H),7.12(s,1H),6.69–6.57(m,2H),5.59(s,2H),3.55(dq,J＝27.2,5.5Hz,5H),1.97–1.80(m,2H),1.17(d,J＝6.2Hz,6H).
13 C NMR(101MHz,CDCl 3 )δ169.0,148.7,131.9,127.1,117.1,116.3,116.2,71.9,67.9,39.1,28.9,22.0.
Preparation example 20
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of cyclopropylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N-cyclopropyl benzamide is obtained by column chromatography separation, and a light brown solid is obtained with the yield of 64%.
1 H NMR(400MHz,CDCl 3 )δ7.22(dt,J＝24.1,8.0Hz,2H),6.70–6.57(m,2H),6.22(s,1H),5.56(s,2H),2.84(dd,J＝7.2,3.6Hz,1H),0.85(d,J＝6.7Hz,2H),0.60(d,J＝4.4Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ170.9,148.7,132.3,127.0,117.3,116.4,115.6,22.8,6.7.
Preparation example 21
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of cyclobutylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, irradiating by 365-375nm ultraviolet light at room temperature, and reacting for 16h. Column chromatography separation gave 2-amino-N-cyclobutylbenzamide as a light brown solid in 74% yield.
1 H NMR(400MHz,CDCl 3 )δ7.30(d,J＝8.1Hz,1H),7.18(t,J＝7.7Hz,1H),6.65(p,J＝7.7Hz,2H),6.22(s,1H),5.50(s,2H),4.53(q,J＝8.1Hz,1H),2.41(s,2H),1.98–1.89(m,2H),1.80–1.73(m,2H).
13 C NMR(101MHz,CDCl 3 )δ168.4,148.7,132.2,127.0,117.2,116.5,116.0,44.8,31.3,15.2.
Preparation example 22
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of cyclopentylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. Column chromatography separation gave 2-amino-N-cyclopentyl benzamide as a light brown solid in 71% yield.
1 H NMR(400MHz,CDCl 3 )δ7.32–7.24(m,1H),7.18(ddd,J＝8.5,7.2,1.5Hz,1H),6.72–6.59(m,2H),5.99(s,1H),5.48(s,2H),4.35(h,J＝6.9Hz,1H),2.14–1.98(m,2H),1.80–1.55(m,4H),1.48(dddd,J＝12.1,10.4,5.6,3.0Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.0,148.5,132.0,127.0,117.2,116.5,116.5,51.3,33.2,23.8.
Preparation example 23
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of cyclohexylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone with the mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N-cyclohexyl benzamide is obtained by column chromatography separation, and a light brown solid is obtained with the yield of 74%.
1 H NMR(400MHz,CDCl 3 )δ7.31–7.25(m,1H),7.23–7.14(m,1H),6.70–6.59(m,2H),5.91(s,1H),5.47(s,2H),3.92(tdt,J＝11.4,8.0,3.9Hz,1H),2.05–1.97(m,2H),1.74(dq,J＝12.0,3.9Hz,2H),1.65(dt,J＝12.8,3.9Hz,1H),1.50–1.30(m,2H),1.23(tdd,J＝12.2,8.4,3.1Hz,3H).
13 C NMR(101MHz,CDCl 3 )δ168.4,148.6,132.0,127.0,117.2,116.7,116.5,48.3,33.2,25.6,24.9.
Preparation example 24
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 2-tetrahydrofurfuryl amine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- ((tetrahydrofuran-2-yl) methyl) benzamide is obtained by column chromatography separation, a yellow oily liquid is obtained, and the yield is 68%.
1 H NMR(400MHz,CDCl 3 )δ7.48–7.04(m,2H),6.69–6.59(m,2H),6.50(s,1H),5.52(s,2H),4.05(qd,J＝7.2,3.2Hz,1H),3.93–3.83(m,1H),3.81–3.65(m,2H),3.32(ddd,J＝13.5,7.2,5.0Hz,1H),2.01(dq,J＝11.8,6.6Hz,1H),1.91(p,J＝6.7Hz,2H),1.67–1.54(m,1H).
13 C NMR(101MHz,CDCl 3 )δ169.3,148.6,132.2,127.2,117.2,116.5,116.0,77.8,68.1,43.1,28.6,25.8.
Preparation example 25
Adding 0.2mmol of 2-nitrobenzaldehyde, 0.8mmol of 4-aminomethyl tetrahydropyran and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N- ((tetrahydro-2H-pyran-4-yl) methyl) benzamide was obtained by column chromatography separation to give a white solid with a yield of 68%.
1 H NMR(400MHz,CDCl 3 )δ7.34–7.25(m,1H),7.20(ddd,J＝8.4,7.2,1.5Hz,1H),6.71–6.60(m,2H),6.25(s,1H),5.49(s,2H),3.98(ddd,J＝11.5,4.5,1.8Hz,2H),3.37(td,J＝11.8,2.1Hz,2H),3.30(t,J＝6.5Hz,2H),1.86(ttt,J＝10.9,7.0,3.8Hz,1H),1.66(dd,J＝12.9,2.0Hz,2H),1.36(qd,J＝11.8,4.5Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ169.5,148.6,132.3,126.9,117.3,116.5,116.1,67.6,45.2,35.4,30.7.
Preparation example 26
Adding 0.2mmol of 4-methyl-2-nitrobenzaldehyde, 0.8mmol of benzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N-benzyl-4-methylbenzamide is obtained by column chromatography separation, and a light brown solid is obtained with the yield of 92%.
1 H NMR(400MHz,CDCl 3 )δ7.36–7.25(m,5H),7.19(d,J＝8.0Hz,1H),6.48–6.37(m,3H),5.51(s,2H),4.54(d,J＝5.7Hz,2H),2.22(s,3H).
13 C NMR(101MHz,CDCl 3 )δ169.1,148.9,142.8,138.4,128.6,127.6,127.3,127.0,117.7,117.5,113.0,43.5,21.3.
Preparation example 27
Adding 0.2mmol of 4, 5-dimethoxy-2-nitrobenzaldehyde, 0.8mmol of benzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of solution of which the mixing ratio of ethyl acetate to acetone is 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. Column chromatography separation gave 2-amino-N-benzyl-4, 5-dimethoxybenzamide as a brown solid in 90% yield.
1 H NMR(400MHz,CDCl 3 )δ7.39–7.19(m,6H),6.85(s,1H),6.46(s,1H),6.18(s,1H),5.43(s,2H),4.56(d,J＝5.6Hz,2H),3.82(d,J＝1.3Hz,3H),3.75(d,J＝1.2Hz,3H).
13 C NMR(101MHz,CDCl 3 )δ168.7,153.3,145.0,140.7,138.6,128.6,127.7,127.3,111.1,106.8,100.7,57.0,55.6,43.6.
Preparation example 28
Adding 0.2mmol of 4-chloro-2-nitrobenzaldehyde, 0.8mmol of benzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2-amino-N-benzyl-4-chlorobenzamide is obtained by column chromatography separation, and brown solid is obtained with the yield of 62 percent.
1 H NMR(400MHz,CDCl 3 )δ7.38–7.23(m,5H),7.21(d,J＝8.3Hz,1H),6.64(d,J＝1.8Hz,1H),6.55(dd,J＝8.4,1.9Hz,1H),6.38(s,1H),5.64(s,2H),4.55(d,J＝5.7Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ168.4,149.9,138.1,138.0,128.7,128.3,127.7,127.6,116.6,116.5,114.0,43.7.
Preparation example 29
Adding 0.2mmol of 6-nitro piperonal, 0.8mmol of benzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 6-amino-N-benzyl benzo [ d ] [1,3] dioxin-5-formamide is obtained by column chromatography separation, and light brown solid is obtained with the yield of 54 percent.
1 H NMR(400MHz,CDCl 3 )δ7.39–7.26(m,6H),6.77(s,1H),6.20(d,J＝1.3Hz,1H),6.16(s,1H),5.85(d,J＝1.3Hz,2H),5.55(s,2H),4.56(d,J＝5.6Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ168.8,151.2,146.4,139.3,138.4,128.7,127.8,127.8,107.0,105.6,101.1,98.1,43.7.
Preparation example 30
Adding 0.2mmol of 3-nitro-2-pyridinecarboxaldehyde, 0.8mmol of benzylamine and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone with the mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 3-amino-N-benzyl pyridine amide is obtained by column chromatography separation, and a yellow oily liquid is obtained with the yield of 20 percent.
1 H NMR(400MHz,CDCl 3 )δ8.45(s,1H),7.83(d,J＝4.1Hz,1H),7.34(d,J＝6.9Hz,4H),7.30–7.23(m,1H),7.14(dd,J＝8.4,4.3Hz,1H),7.03–6.96(m,1H),5.97(s,2H),4.61(d,J＝6.1Hz,2H).
13 C NMR(101MHz,CDCl 3 )δ167.6,145.6,138.5,136.8,130.0,128.6,127.7,127.3,127.2,124.8,42.9.
Preparation example 31
Adding 0.2mmol of 3-nitro-2-pyridineformaldehyde, 0.8mmol of p-hydroxyphenylglycine methyl ester and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of which the mixing ratio of ethyl acetate to acetone is 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 2- (2-aminobenzamide) -2- (4-hydroxyphenyl) acetate is obtained by column chromatography separation, and light yellow oily liquid is obtained with the yield of 34 percent.
1 H NMR(400MHz,CDCl 3 )δ7.45(dd,J＝8.3,1.5Hz,1H),7.28–7.14(m,3H),7.09(d,J＝6.6Hz,1H),6.78–6.63(m,4H),5.60(d,J＝6.6Hz,1H),5.48(s,2H),3.75(s,3H).
13 C NMR(101MHz,CDCl 3 )δ171.9,168.6,156.4,148.8,132.8,128.5,128.0,127.6,117.5,116.9,115.9,115.0,56.2,52.9.
Preparation example 32
Adding 0.2mmol of 3-nitro-2-pyridinecarboxaldehyde, 0.8mmol of 1-aminocyclopropylmethyl formate and 0.4mmol of acetic acid into a 10mL reaction tube, adding 3.0mL of a solution of ethyl acetate and acetone in a mixing ratio of 6 as a solvent, and irradiating by 365-375nm ultraviolet light at room temperature for reacting for 16h. The 1- (2-aminobenzamide) cyclopropane-1-methyl formate was obtained by column chromatography separation, and a yellow solid was obtained with a yield of 58%.
1 H NMR(400MHz,CDCl 3 )δ7.33(dd,J＝7.9,1.5Hz,1H),7.20(ddd,J＝8.4,7.1,1.5Hz,1H),6.74(s,1H),6.69–6.57(m,2H),5.56(s,1H),3.69(s,3H),1.64(q,J＝4.7Hz,2H),1.32–1.16(m,2H).
13 C NMR(101MHz,CDCl 3 )δ173.0,170.3,148.9,132.6,127.4,117.3,116.4,115.1,52.5,33.7,17.6.
Claims (6)
1. A method for synthesizing 2-aminobenzamide compounds by ultraviolet light induction is characterized in that the synthesis method of the 2-aminobenzamide compounds III is as follows:
taking a 2-nitrobenzaldehyde compound I and primary amine II as raw materials, taking a mixed solution of ethyl acetate and acetone as a solvent in the presence of acetic acid, and carrying out dehydrogenation N-acylation reaction and nitro reduction reaction under ultraviolet irradiation in a room temperature environment to obtain a 2-aminobenzamide compound III; the ultraviolet wavelength is 350-380nm; ethyl acetate/acetone was 4.
2. The method for synthesizing the 2-aminobenzamide compound under the induction of ultraviolet light according to claim 1, wherein: the 2-nitrobenzaldehyde compound I has a structure shown in a formula 1:
wherein Ar is various substituted phenyl groups and various substituted pyridine ring groups.
3. The method for synthesizing the 2-aminobenzamide compound under the induction of ultraviolet light according to claim 1, wherein: the primary amine II has a structure shown in a formula 2:
R-NH 2
formula 2
Wherein R is C 3 ～C 12 Aliphatic hydrocarbon group of (C) 3 ～C 6 The compound is a compound of the following formula (I), wherein the compound is a cycloalkyl, various substituted phenyl, various substituted benzyl, various substituted heterocyclic groups and various amino acid ester groups.
4. The method for synthesizing the 2-aminobenzamide compound under the induction of ultraviolet light according to claim 1, wherein: the 2-aminobenzamide compound III has a structure shown in a formula 3:
wherein Ar is various substituted phenyl groups and various substituted pyridine ring groups; r is C 3 ～C 12 Aliphatic hydrocarbon group of (C) 3 ～C 6 The aryl group of the formula (I) is a cycloalkyl group, various substituted phenyl groups, various substituted benzyl groups, various substituted heterocyclic groups and various amino acid ester groups.
5. The method for synthesizing the 2-aminobenzamide compound under the induction of ultraviolet light according to claim 1, wherein: the molar weight of the primary amine is 2 to 4 times of that of the 2-nitrobenzaldehyde compound; the molar weight of the acetic acid is 0.5 to 2 times of that of the 2-nitrobenzaldehyde compound.
6. The method for synthesizing the 2-aminobenzamide compound under the induction of ultraviolet light according to any one of claims 1 to 5, characterized in that: the reaction conditions are as follows: and (3) irradiating the mixture by using an ultraviolet lamp of 24-26W at room temperature for 14-18 h.
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