CN107445784A - A kind of solvent-free aryl propionitrile of 2 p-nitrophenyl 3 and preparation method thereof - Google Patents
A kind of solvent-free aryl propionitrile of 2 p-nitrophenyl 3 and preparation method thereof Download PDFInfo
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- CN107445784A CN107445784A CN201610382233.1A CN201610382233A CN107445784A CN 107445784 A CN107445784 A CN 107445784A CN 201610382233 A CN201610382233 A CN 201610382233A CN 107445784 A CN107445784 A CN 107445784A
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- C—CHEMISTRY; METALLURGY
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract
The invention discloses a kind of solvent-free aryl propionitrile of 2 p-nitrophenyl 3 and preparation method thereof, first adds 4 nitrobenzene ethane nitriles, aromatic aldehyde, alkali and dihydropyridine ester in reaction tube, stirring reaction；Secondly column chromatography, the stationary phase that column chromatography uses is silicagel column, produces the aryl propionitrile of 2 p-nitrophenyl of product 3.The present invention solves the problems, such as that prior art is uneconomical, not environmentally and the reaction time is longer using solvent, it compensate for directly using 4 nitrobenzene ethane nitriles and aldehyde as substrate, be the technological gap that hydrogen source prepares the aryl propionitrile of 2 p-nitrophenyl 3 under condition of no solvent by dihydropyridine ester；Knoevenagel and reduction two-step reaction are together in series by one kettle way, simplify reactions steps, can efficiently obtain target product.And the present invention, relative to traditional hydrogen source, has the advantages of nontoxic, reaction condition is gentle, chemo-selective is high using dihydropyridine ester as hydrogen source.
Description
Technical field
The invention belongs to technical field of chemistry and chemical engineering, more particularly to a kind of solvent-free 2- p-nitrophenyls -3- aryl propionitrile
And preparation method thereof.
Background technology
2- p-nitrophenyl -3- aryl propionitrile is a kind of important medicine intermediate, and the itrile group in molecule can be easy to
Be converted into other functional groups, such as carboxylic acid, amino, ketone, nitro can also be readily converted to amino.So this kind of chemical combination
The preparation of thing has critically important practical value.The method for directly preparing such compound at present mainly has three kinds：First, pass through
Dihydropyridine ester Knoevenagel products of selective reduction 4- nitrobenzene ethane nitriles and aldehyde on the spot.But this method needs to utilize
Reaction dissolvent water, alcohol or dimethyl sulfoxide (DMSO) are solvent and cocatalyst.Second, using water as solvent, it is not necessary to add any urge
Agent, using the Knoevenagel products of 4- nitrobenzene ethane nitriles and aldehyde as substrate, selective reduction is carried out using dihydropyridine ester.
But this method can not be prepared directly using 4- nitrobenzene ethane nitriles and aldehyde as substrate one kettle way.In addition, some conventional hydrogen sources, example
Such as H2、NaBH4、NaBH3CN, alcohol, diimine, PhSiH3Hydrogen source is used as etc. the reduction that can also be applied to double bond, but using these materials
Reduction reaction have the shortcomings that severe reaction conditions, chemo-selective are low, need expensive catalyst.Recently, coenzyme NAD H
Analog dihydropyridine ester be taken seriously as a kind of new hydrogen source, relative to traditional hydrogen source, it has nontoxic, reaction bar
The advantages that part is gentle, chemo-selective is high.Up to the present, directly using 4- nitrobenzene ethane nitriles and aldehyde as substrate, dihydropyridine ester
2- p-nitrophenyl -3- aryl propionitrile is prepared for hydrogen source, under condition of no solvent to have not been reported.
Prior art is uneconomical, not environmentally and the reaction time is longer using solvent.
The content of the invention
It is an object of the invention to provide a kind of solvent-free 2- p-nitrophenyls -3- aryl propionitrile and preparation method thereof, purport
Solving the problems, such as that prior art is uneconomical, not environmentally and the reaction time is longer using solvent.
The present invention is achieved in that a kind of preparation method of solvent-free 2- p-nitrophenyls -3- aryl propionitrile, the nothing
The preparation method of solvent 2- p-nitrophenyl -3- aryl propionitrile includes：
4- nitrobenzene ethane nitriles, aromatic aldehyde, alkali and dihydropyridine ester are added in reaction tube first, stirring reaction；
Secondly column chromatography, the stationary phase that column chromatography uses is silicagel column, produces product 2- p-nitrophenyl -3- arylprops
Nitrile.
Further, the mol ratio of aromatic aldehyde and the 4- nitrobenzene ethane nitrile is 1：1-1：2；Aromatic aldehyde and dihydropyridine ester
Mol ratio is 1：1-1：2, the mol ratio of aromatic aldehyde and alkali is 1：0.2~1:2.
Further, described to add 4- nitrobenzene ethane nitriles, aromatic aldehyde, alkali and dihydropyridine ester in reaction tube, heating rises
Temperature is to 70-100 DEG C, and stirring reaction 0.5-4h.
Further, the silicagel column mobile phase is by petroleum ether and ethyl acetate volume ratio 15:1~5:1.
Another object of the present invention is to provide a kind of preparation side of the solvent-free 2- p-nitrophenyls -3- aryl propionitrile
Solvent-free 2- p-nitrophenyls -3- aryl propionitrile prepared by method, the solvent-free 2- p-nitrophenyls -3- aryl propionitrile include：
Aromatic aldehyde, 4- nitrobenzene ethane nitriles, dihydropyridine ester and alkali；
The mol ratio of aromatic aldehyde, 4- nitrobenzene ethane nitriles and dihydropyridine ester is 1：1.2：1.2, the mol ratio of aromatic aldehyde and alkali
For 1：0.2~1:2.
Further, the alkali is organic base or inorganic base.
Further, the general structure of the aromatic aldehyde is：
Wherein described R1 includes-Ph, -4-CH3Ph, -4-CH3OPh, -4-FPh, -4-ClPh, -4-CNPh, -4-BrPh, -
2-NO2Ph, -3-NO2Ph, -4-NO2Ph, 2-furyl, reaction equation are as follows：
The preparation method of solvent-free 2- p-nitrophenyls -3- aryl propionitrile provided by the invention, solving prior art needs
To use solvent it is uneconomical, not environmentally and the problem of the reaction time is longer, compensate for directly using 4- nitrobenzene ethane nitriles and aldehyde as
Substrate, it is the technological gap that hydrogen source prepares 2- p-nitrophenyl -3- aryl propionitrile under condition of no solvent by dihydropyridine ester；
Knoevenagel and reduction two-step reaction are together in series by one kettle way, simplify reactions steps, can efficiently obtain target production
Thing.And the present invention, using dihydropyridine ester as hydrogen source, relative to traditional hydrogen source, it has, and nontoxic, reaction condition is gentle, chemistry
The advantages that selectivity is high.
It is provided by the invention using dihydropyridine ester as hydrogen source, under condition of no solvent prepare 2- p-nitrophenyl -3- arylprops
The method of nitrile, solve the problems, such as prior art need to use solvent, reaction time it is longer (reaction time 24h,
Tetrahedron Letters 51(2010)5246–5251).It compensate for directly using 4- nitrobenzene ethane nitriles and aldehyde as substrate, lead to
Cross the technological gap that dihydropyridine ester prepares 2- p-nitrophenyl -3- aryl propionitrile for hydrogen source under condition of no solvent；One kettle way
Knoevenagel and reduction two-step reaction are together in series, simplify reactions steps, up to 95% target production can be obtained
Thing.
Brief description of the drawings
Fig. 1 is the preparation method flow chart of solvent-free 2- p-nitrophenyls -3- aryl propionitrile provided in an embodiment of the present invention.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention
It is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to
Limit the present invention.
The application principle of the present invention is explained in detail below in conjunction with the accompanying drawings.
The solvent-free 2- p-nitrophenyls -3- aryl propionitrile of the embodiment of the present invention includes：Aromatic aldehyde, 4- nitrobenzene ethane nitriles,
Dihydropyridine ester and alkali；The mol ratio of aromatic aldehyde, 4- nitrobenzene ethane nitriles and dihydropyridine ester is 1：1.2：1.2, aromatic aldehyde and alkali
Mol ratio be 1：0.2~1:2.
The general structure of the aromatic aldehyde is：
Wherein described R1 includes-Ph, -4-CH3Ph, -4-CH3OPh, -4-FPh, -4-ClPh, -4-CNPh, -4-BrPh, -
2-NO2Ph, -3-NO2Ph, -4-NO2Ph, 2-furyl, reaction equation are as follows：
As shown in figure 1, the preparation method of the solvent-free 2- p-nitrophenyls -3- aryl propionitrile of the embodiment of the present invention include with
Lower step：
S101：4- nitrobenzene ethane nitriles, aromatic aldehyde, alkali and dihydropyridine ester are added in reaction tube first, aromatic aldehyde, 4-
The mol ratio of nitrobenzene ethane nitrile and dihydropyridine ester is 1：1.2：1.2, the mol ratio of aromatic aldehyde and alkali is 1：0.2~1:2, heating
70-100 DEG C is warming up to, and in stirring reaction 0.5-4h at this temperature；
S102：Secondly column chromatography, the stationary phase that column chromatography uses is silicagel column, and mobile phase is pressed by petroleum ether and ethyl acetate
According to volume ratio 15:1~5:1 prepares, and produces product 2- p-nitrophenyl -3- aryl propionitrile.
Reducing agent is dihydropyridine ester.
The alkali can be organic base (TEA, DEAE, TEOA, DABCO) or inorganic base (NaHCO3、Na2CO3、
K2CO3, NaOH, KOH), the mol ratio of aromatic aldehyde and alkali is 1：0.2~1:2.
The application effect of the present invention is explained in detail with reference to specific embodiment.
Embodiment 1：
1st, by aldehyde 1 (p-bromobenzaldehyde, 21.2mg, 0.2mmol), 4- nitrobenzene ethane nitriles (38.9mg, 0.24mmol), dihydro
Pyridine ester (60.7mg, 0.24mmol), DEAE (8.2mg, 0.08mmol, 0.4eq) are added in 10mL reaction tubes, are warming up to
100 degree, stirring reaction 4 hours, then silicagel column column chromatography (petroleum ether：Ethyl acetate=10:1) product 62.2mg, yield, are obtained
94%, red solid.
2nd, synthetic method of the invention
By aromatic aldehyde 1 (0.2mmol), 4- nitrobenzene ethane nitriles 2 (0.24mmol, 27.1mg), dihydropyridine ester (0.24mol,
60.7), alkali is added in 10mL reaction tubes, heating, stirring reaction to certain time, then silicagel column column chromatography (petroleum ether：Second
Acetoacetic ester=10:1 elution) after, it is final to obtain product.
3rd, in synthetic method alkali screening
According to the method for synthesis, temperature is 100 degree, and the reaction time is 12 hours, and the mol ratio of aldehyde and alkali is 1：0.1,
In the presence of variety classes alkali, with p-bromobenzaldehyde and the reaction of 4- nitrobenzene ethane nitriles for template reaction, as a result as shown in table 1.
The screening of base reagent in 1 synthetic method of the present invention of table
As a result show, when the synthetic method of the present invention adds alkali in reaction raw materials, yield, which is substantially better than, is not added with alkali
Synthetic method.Wherein, DEAE best results.
4th, in synthetic method the dosage of alkali screening
According to the method for synthesis, temperature is 100 degree, and the reaction time is 12 hours, using DEAE as alkali, investigation aldehyde and alkali
Mol ratio, in the base amount of different mol ratio, reaction result is as shown in table 2.As a result show, when the mol ratio for investigating aldehyde and alkali
For 1：To be best when 0.4.
The screening of the dosage of alkali in 2 synthetic method of the present invention of table
| Numbering | The mol ratio of aldehyde and alkali | Yield (%) |
| 1 | 1：0.1 | 75 |
| 2 | 1：0.2 | 84 |
| 3 | 1：0.4 | 92 |
| 4 | 1：0.5 | 90 |
| 5 | 1：0.8 | 88 |
| 6 | 1：1 | 83 |
5th, in synthetic method the reaction time screening
According to the method for synthesis, temperature is 100 degree, and using DEAE as alkali, the mol ratio of aldehyde and alkali is 1：0.4, investigate anti-
Between seasonable, reaction result is as shown in table 3.It is 2 hours to react optimum reacting time.
The screening of 3 synthesising reacting time of the present invention of table
6th, in synthetic method reaction temperature screening
According to the method for synthesis, using DEAE as alkali, the mol ratio of aldehyde and alkali is 1：0.4, the reaction time is 2 hours, is examined
Reaction temperature is examined, reaction result is as shown in table 4.It is 90 degree to react optimum temperature.
The screening of 4 synthesis reaction temperature of the present invention of table
| Numbering | Temperature/DEG C | Yield (%) |
| 1 | 60 | 0 |
| 2 | 70 | 0 |
| 3 | 80 | 75 |
| 4 | 90 | 93 |
| 5 | 100 | 92 |
7th, 2- p-nitrophenyl -3- aryl propionitrile is prepared
According to the method for synthesis, using DEAE as alkali, the mol ratio of aldehyde and alkali is 1：0.4, the reaction time is 2 hours, instead
It is 90 degree to answer temperature, prepares the different 2- p-nitrophenyl -3- aryl propionitrile of series, and reaction result is as shown in table 5.
The preparation result of the 2- p-nitrophenyl -3- aryl propionitrile of table 5
| Products nr | R | Yield (%) |
| 1 | C6H5 | 85 |
| 2 | 4-MeC6H4 | 85 |
| 3 | 4-MeOC6H4 | 92 |
| 4 | 4-FC6H4 | 95 |
| 5 | 4-ClC6H4 | 92 |
| 6 | 4-NCC6H4 | 94 |
| 7 | 4-NO2C6H4 | 92 |
| 8 | 2-NO2C6H4 | 86 |
| 9 | 3-NO2C6H4 | 92 |
| 10 | 1-Naphthyl | 91 |
| 11 | 2-fruyl | 96 |
8th, the specific physical-chemical data of portion of product is as follows：
Product -1：1HNMR(600MHz,CDCl3):3.12 (dd, J=6.72,13.88Hz, 1H), 3.20 (dd, J=
7.66,13.60Hz, 1H), 4.08 (t, J=7.14Hz, 1H), 7.00-7.04 (m, 2H), 7.22 (d, J=5.76Hz, 3H),
7.30 (d, J=8.22Hz, 2H), 8.14 (d, J=8.16Hz, 2H).
Product -2：1HNMR(400MHz,CDCl3):2.33 (s, 3H), 3.16 (dd, J=6.74,13.62Hz, 1H), 3.26
(dd, J=7.54,13.56Hz, 1H), 4.16 (t, J=7.52Hz, 1H), 6.96 (d, J=7.96Hz, 2H), 7.10 (d, J=
7.86Hz, 2H), 7.42 (d, J=8.68Hz, 2H), 8.20 (d, J=8.76Hz, 2H).
Product -4：1HNMR(400MHz,CDCl3):3.16-3.26 (m, 2H), 4.14 (t, J=6.92Hz, 1H), 6.98-
7.10 (m, 2H), 7.42 (d, J=8.446Hz, 2H), 8.26 (d, J=8.36Hz, 2H).
Product -6：1HNMR(400MHz,CDCl3):3.32 (d, J=7.08Hz, 2H), 4.23 (t, J=7.08Hz, 1H),
7.26 (d, J=8.18Hz, 2H), 7.46 (d, J=8.64Hz, 2H), 7.64 (d, J=8.16Hz, 2H), 8.24 (d, J=
8.60Hz,2H)。
Product -7：1HNMR(400MHz,CDCl3):3.34 (d, J=7.08Hz, 2H), 4.26 (t, J=7.06Hz, 1H),
7.30 (d, J=8.52Hz, 2H), 7.44 (d, J=8.54Hz, 2H), 8.22 (d, J=8.48Hz, 2H), 8.26 (d, J=
8.64Hz,2H)。
Product -9：1HNMR(400MHz,CDCl3):3.33 (d, J=7.24Hz, 2H), 4.24 (t, J=7.26Hz, 1H),
7.51-7.59 (m, 4H), 8.06 (s, 1H), 8.22 (d, J=7.96Hz, 1H), 8.28 (d, J=8.54Hz, 2H).
Product -10：1HNMR(400MHz,CDCl3):3.56-3.64 (m, 1H), 3.73-3.82 (m, 1H), 4.32 (t, J=
7.66Hz, 1H), 7.22 (d, J=6.98Hz, 1H), 7.36-7.42 (m, 3H), 7.52-7.62 (m, 2H), 7.84-7.98 (m,
3H), 8.22 (d, J=8.68Hz, 2H).
Product -11：1HNMR(400MHz,CDCl3):3.22 (dd, J=7.16,14.84Hz, 1H), 3.36 (dd, J=
7.44,14.86Hz, 1H), 4.30 (t, J=7.28Hz, 1H), 6.10 (d, J=3.16Hz, 1H), 6.31 (t, J=3.04Hz,
1H), 7.38 (d, J=1.36Hz, 1H), 7.46 (d, J=8.46Hz, 2H), 8.24 (d, J=8.46Hz, 2H).
As a result show, method of the invention can synthesize a variety of 2- p-nitrophenyls -3- aryl propionitrile, most of product production
Rate is more than 90%.In summary, first using aldehyde, 4- nitrobenzene ethane nitriles and dihydropyridine ester as raw material, one kettle way is carried out the present invention
Reaction, without any solvent, can efficiently synthesize 2- p-nitrophenyl -3- aryl propionitrile in the short time, be a kind of simple, high
The preparation method of effect, green.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
All any modification, equivalent and improvement made within refreshing and principle etc., should be included in the scope of the protection.
Claims (7)
1. a kind of preparation method of solvent-free 2- p-nitrophenyls -3- aryl propionitrile, it is characterised in that the solvent-free 2- is to nitre
The preparation method of base phenyl -3- aryl propionitrile includes：
4- nitrobenzene ethane nitriles, aromatic aldehyde, alkali and dihydropyridine ester are added in reaction tube first, stirring reaction；
Secondly column chromatography, the stationary phase that column chromatography uses is silicagel column, produces product 2- p-nitrophenyl -3- aryl propionitrile.
2. the preparation method of solvent-free 2- p-nitrophenyls -3- aryl propionitrile as claimed in claim 1, it is characterised in that institute
The mol ratio for stating aromatic aldehyde, 4- nitrobenzene ethane nitriles and dihydropyridine ester is 1：1.2：1.2, the mol ratio of aromatic aldehyde and alkali is 1：
0.2~1:2.
3. the preparation method of solvent-free 2- p-nitrophenyls -3- aryl propionitrile as claimed in claim 1, it is characterised in that institute
State and add 4- nitrobenzene ethane nitriles, aromatic aldehyde, alkali and dihydropyridine ester in reaction tube, be heated to 70-100 DEG C, and stir
Mix reaction 0.5-4h.
4. the preparation method of solvent-free 2- p-nitrophenyls -3- aryl propionitrile as claimed in claim 1, it is characterised in that institute
Silicagel column mobile phase is stated by petroleum ether and ethyl acetate volume ratio 15:1~5:1.
5. a kind of preparation method of solvent-free 2- p-nitrophenyls -3- aryl propionitrile as claimed in claim 1 prepares solvent-free
2- p-nitrophenyl -3- aryl propionitrile, it is characterised in that the solvent-free 2- p-nitrophenyls -3- aryl propionitrile includes：Fragrance
Aldehyde, 4- nitrobenzene ethane nitriles, dihydropyridine ester and alkali；
The mol ratio of aromatic aldehyde, 4- nitrobenzene ethane nitriles and dihydropyridine ester is 1：1.2：1.2, the mol ratio of aromatic aldehyde and alkali is 1：
0.2~1:2.
6. solvent-free 2- p-nitrophenyls -3- aryl propionitrile as claimed in claim 5, it is characterised in that the alkali is organic
Alkali or inorganic base.
7. solvent-free 2- p-nitrophenyls -3- aryl propionitrile as claimed in claim 5, it is characterised in that the aromatic aldehyde
General structure is：
Wherein described R1 includes-Ph, -4-CH3Ph, -4-CH3OPh, -4-FPh, -4-ClPh, -4-CNPh, -4-BrPh, -2-
NO2Ph, -3-NO2Ph, -4-NO2Ph, 2-furyl, reaction equation are as follows：
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1433401A (en) * | 1999-12-03 | 2003-07-30 | 阿斯特拉曾尼卡有限公司 | New phenalkyloxy-phenyl derivatives |
| CN103467223A (en) * | 2013-09-16 | 2013-12-25 | 西华大学 | Green conjugated double bond reduction method |
| CN105061257A (en) * | 2015-09-08 | 2015-11-18 | 西华大学 | Method for selectively reducing 4-nitrophenylacetonitrile/aldehyde condensation reaction product |
-
2016
- 2016-06-01 CN CN201610382233.1A patent/CN107445784A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1433401A (en) * | 1999-12-03 | 2003-07-30 | 阿斯特拉曾尼卡有限公司 | New phenalkyloxy-phenyl derivatives |
| CN103467223A (en) * | 2013-09-16 | 2013-12-25 | 西华大学 | Green conjugated double bond reduction method |
| CN105061257A (en) * | 2015-09-08 | 2015-11-18 | 西华大学 | Method for selectively reducing 4-nitrophenylacetonitrile/aldehyde condensation reaction product |
Non-Patent Citations (2)
| Title |
|---|
| BISWAJITA BARUAH，等: "Synthesis of 5-alkylated barbituric acids and 3-alkylated indoles via microwave-assisted three-component reactions in solvent-free conditions using Hantzsch 1,4-dihydropyridines as reducing agents", 《MOL DIVERS》 * |
| ZE ZHANG，等: "Solvent-free mechanochemical and one-pot reductive benzylizations of malononitrile and 4-methylaniline using Hantzsch 1,4-dihydropyridine as the reductant", 《ORG.BIOMOL.CHEM》 * |
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