CN111995525A - Preparation method of arylamine compound - Google Patents

Preparation method of arylamine compound Download PDF

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CN111995525A
CN111995525A CN202010902430.8A CN202010902430A CN111995525A CN 111995525 A CN111995525 A CN 111995525A CN 202010902430 A CN202010902430 A CN 202010902430A CN 111995525 A CN111995525 A CN 111995525A
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冯秀娟
耿羽轩
包明
陈冲
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Dalian University of Technology
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    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
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Abstract

The invention belongs to the technical field of natural compounds, pharmaceutical and chemical intermediates and related chemistry, and provides a preparation method of arylamine compounds. The adopted catalyst is a nano porous platinum iron catalyst, the pore size is 1-50 nm, and the molar ratio of the aromatic nitro compound to the used catalyst is 1: 0.01-1: 0.5; the pressure of the hydrogen is 0.1-20.0 MPa; the molar concentration of the nitro compound in the solvent is 0.01-2 mmol/mL. The method has the advantages of very mild reaction conditions, high product selectivity, simple operation and post-treatment, high catalyst activity, stable property, low price, good reproducibility, repeated utilization and no obvious reduction of the catalytic effect, and provides possibility for realizing industrialization.

Description

Preparation method of arylamine compound
Technical Field
The invention belongs to the technical field of natural compounds, pharmaceutical and chemical intermediates and related chemistry, and relates to a preparation method of arylamine compounds.
Background
The arylamine compound is an important intermediate in organic synthesis and is widely applied to synthesis of fine chemicals such as organic azo dyes, sulfonamides and the like. The main method for obtaining arylamine in industrial production is the selective catalytic hydrogenation reduction of aromatic nitro compound.
The reduction method of the aromatic nitro compound mainly comprises a metal reduction method, a sodium sulfide reduction method, an electrochemical reduction method and a transition metal catalytic reduction method. The metal reduction method needs equivalent metal and hydrochloric acid, the corrosion resistance of equipment is high in reaction, a large amount of metal waste residues are generated in the reaction process, a large amount of salt-containing wastewater needs to be discharged, the method does not conform to the concept of green chemistry, and the method is basically not used in industrial production. A large amount of sulfate is generated in the reaction of the sodium sulfide reduction method, so that a large amount of waste liquid is generated, and the treatment cost is increased. The electrochemical reduction method needs special electrochemical equipment and has high energy consumption. The transition metal catalytic reduction method mainly comprises homogeneous catalysis and heterogeneous catalysis. Wherein, the homogeneous catalyst has high price, difficult separation and difficult recycling, and the obtained product has metal ion residue; the catalyst used in heterogeneous catalysis is mainly a supported metal nanoparticle catalyst, and the catalytic effect of the catalyst can be influenced by active components, auxiliaries, carriers and different reduction methods of the catalyst.
The nano porous platinum iron material is a novel nano structure catalyst, consists of nano-scale pore channels and ligaments, and has the advantages of extremely large specific surface area, excellent electric and thermal conductivity and no toxicity. Can show completely different physical and chemical properties from bulk metal, and is a research hotspot in the field of catalysis. The nano porous platinum iron (PtFeNPore) catalyst has the advantages of low price, simple preparation, high catalytic activity, stable property, easy recycling and the like.
Disclosure of Invention
The invention provides a preparation method of arylamine compounds, the reaction conditions of the method are very mild, the selected catalyst has the advantages of high activity, stable property, low price, high chemical selectivity and the like, and the catalytic activity is not obviously reduced after the catalyst is recycled for many times.
The technical scheme of the invention is as follows:
a preparation method of arylamine compounds takes aromatic nitro compounds as raw materials, nano-porous platinum iron catalyst (PtFeNPore) as a catalyst, hydrogen as a hydrogen source, and aromatic amines are prepared by selective hydrogenation in a solvent, wherein the synthetic route is as follows:
Figure BDA0002660217550000021
the reaction temperature is 25-100 ℃, and the reaction time is 10-50 h;
R1selected from the group consisting of hydrogen, alkyl, methoxy, hydroxy, halogen, phenoxy, amino, carbethoxy and methylmercapto;
R2selected from the group consisting of hydrogen, alkyl, methoxy, hydroxy, halogen, phenoxy, amino, carbethoxy and methylmercapto;
R1and R2The same or different;
wherein the nano-porous platinum-iron catalyst (PtFeNPore) has a pore size of 1-50 nm, and the molar ratio of the aromatic nitro compound to the nano-porous platinum-iron catalyst is 1: 0.01-1: 0.5;
the pressure of the hydrogen is 0.1-20.0 MPa;
the molar concentration of the aromatic nitro compound in the solvent is 0.01-2 mmol/mL;
the solvent is one of methanol, toluene, cyclohexane, dichloromethane, dichloroethane, N-dimethylformamide, tert-butyl alcohol, dimethyl ether, ethyl acetate, ethylene glycol dimethyl ether, tetrahydrofuran, acetone or ethanol;
the separation method comprises the following steps: recrystallization, column chromatography, and the like. Solvents used for the recrystallization method, such as chloroform, cyclohexane, dioxane, benzene, toluene, ethanol, petroleum ether, acetonitrile, N-dimethylformamide, tetrahydrofuran, ethyl acetate; by column chromatography, silica gel or basic alumina can be used as stationary phase, and the developing agent is generally polar and nonpolar mixed solvent, such as ethyl acetate-petroleum ether, ethyl acetate-n-hexane, dichloromethane-petroleum ether, and methanol-petroleum ether.
The method has the advantages of very mild reaction conditions, high product selectivity, simple operation and post-treatment, good catalyst reproducibility, repeated utilization of the catalyst for multiple times, no obvious reduction of the catalytic effect, and possibility for realizing industrialization. Under the same reaction conditions, the nano-porous palladium (PdNPore) and a commercial supported platinum-carbon (5% Pt/C) catalyst have low chemical selectivity, and when the aromatic nitro compound contains halogen, dehalogenation reaction can occur.
Drawings
FIG. 1 is a schematic representation of 4-methylaniline of examples 1, 21H nuclear magnetic spectrum.
FIG. 2 is the 2- (4-aminophenyl) acetonitrile of example 3, 41H nuclear magnetic spectrum.
FIG. 3 is a diagram of 4-methoxyaniline of example 5, 61H nuclear magnetic spectrum.
FIG. 4 is ethyl 4-aminobenzoate from examples 7, 81H nuclear magnetic spectrum.
FIG. 5 is a representation of 4-bromoaniline from examples 9,10,11,12,13,141H nuclear magnetic spectrum.
FIG. 6 shows the preparation of anilines according to examples 11,12,13 and 141H nuclear magnetic spectrum.
Detailed Description
The following further describes a specific embodiment of the present invention with reference to the drawings and technical solutions.
The preparation method of the arylamine compound has the advantages that the highest selectivity and the reaction yield respectively reach 100 percent and 95 percent, the selected catalyst has good catalytic reaction repeatability, the operation and the post-treatment are simple, the catalytic effect is not obviously reduced after repeated utilization, and favorable conditions are provided for the industrial production of the arylamine compound.
The invention will be further illustrated with reference to the following specific examples. The simple replacement or improvement of the present invention by those skilled in the art is within the technical scheme of the present invention.
Example 1: synthesis of 4-methylaniline
To a methanol (3mL) solvent added with PtFeNPore (3.6mg,5 mol%) catalyst, substrate 4-nitrotoluene (69.07mg,0.5mmol) and hydrogen (0.1MPa) were added, and the mixture was reacted on a magnetic stirrer at 25 ℃ for 24 hours, and column chromatography (silica gel, 200 mesh, 300 mesh; developing solvent, petroleum ether) was carried out to obtain 63.54mg of 4-methylaniline with a yield of 92%.
Figure BDA0002660217550000041
A white solid;1H NMR(400MHz,CDCl3):6.96(d,J＝8.0Hz,2H),6.60(d,J＝8.1Hz,2H),3.51(s,2H),2.23(s,3H).
example 2: synthesis of 4-methylaniline
To a solvent of PtFeNPore (7.2mg,10 mol%) added with a catalyst in dichloromethane (3mL), a substrate of 4-nitrotoluene (69.07mg,0.5mmol) and hydrogen (1MPa) were added, the mixture was reacted at 50 ℃ for 15 hours on a magnetic stirrer, and column chromatography (silica gel, 200 mesh, 300 mesh; developing solvent, petroleum ether: ethyl acetate ═ 10: 1) was performed to obtain 62.85mg of 4-methylaniline, with a yield of 91%.
Figure BDA0002660217550000042
A white solid;1H NMR(400MHz,CDCl3):6.96(d,J＝8.0Hz,2H),6.60(d,J＝8.1Hz,2H),3.51(s,2H),2.23(s,3H).
example 3: synthesis of 2- (4-aminophenyl) acetonitrile
To a solvent of PtFeNPore (4.3mg,6 mol%) in toluene (3mL) added with a catalyst, a substrate of 2- (4-nitrophenyl) acetonitrile (81.08mg,0.5mmol) and hydrogen (0.1MPa) were added, and the mixture was reacted at 25 ℃ for 24 hours on a magnetic stirrer, and column chromatography (silica gel, 200 mesh and 300 mesh; developing solvent, petroleum ether: ethyl acetate ═ 10: 1) was performed to obtain 73.78mg of 2- (4-aminophenyl) acetonitrile in a yield of 91%.
Figure BDA0002660217550000051
A light yellow solid;1H NMR(400MHz,CDCl3):7.08(d,J＝8.5Hz,2H),6.66(d,J＝8.4Hz,2H),3.73(s,2H),3.61(s,2H).
example 4: synthesis of 2- (4-aminophenyl) acetonitrile
To an ethyl acetate (3mL) solvent to which PtFeNPore (6.5mg,9 mol%) as a catalyst was added, a substrate, 2- (4-nitrophenyl) acetonitrile (81.08mg,0.5mmol), hydrogen (10MPa), was added, and the mixture was reacted at 50 ℃ for 10 hours on a magnetic stirrer, and column chromatography (silica gel, 200-mesh 300; developing solvent, petroleum ether: ethyl acetate ═ 10: 1) was performed to obtain 73.78mg of 2- (4-aminophenyl) acetonitrile in a yield of 91%.
Figure BDA0002660217550000052
A light yellow solid;1H NMR(400MHz,CDCl3):7.08(d,J＝8.5Hz,2H),6.66(d,J＝8.4Hz,2H),3.73(s,2H),3.61(s,2H).
example 5: synthesis of 4-methoxyaniline
To a solvent of PtFeNPore (3.6mg,5 mol%) in methanol (6mL) with catalyst added, substrate 4-methoxynitrobenzene (76.57mg,0.5mmol) and hydrogen (0.1MPa) were added, and the mixture was reacted for 15h at 80 ℃ on a magnetic stirrer, and column chromatography (silica gel, 200 mesh 300; developing solvent, petroleum ether: ethyl acetate: 10: 1) was carried out to obtain 69.68mg of 4-methoxyaniline, 91% yield.
Figure BDA0002660217550000061
A colorless solid;1H NMR(400MHz,CDCl3):6.81–6.71(m,2H),6.70–6.59(m,2H),3.75(s,3H),3.37(s,2H).
example 6: synthesis of 4-methoxyaniline
To an acetonitrile (3mL) solvent added with PtFeNPore (7.2mg,10 mol%) catalyst, a substrate of 4-methoxynitrobenzene (76.57mg,0.5mmol) and hydrogen (1MPa) are added, the mixture is placed on a magnetic stirrer to react for 5h at 100 ℃, and column chromatography (silica gel, 200 meshes and 300 meshes; developing agent, petroleum ether: ethyl acetate: 10: 1) is carried out to obtain 71.21mg of 4-methoxyaniline with the yield of 93%.
Figure BDA0002660217550000062
A colorless solid;1H NMR(400MHz,CDCl3):6.81–6.71(m,2H),6.70–6.59(m,2H),3.75(s,3H),3.37(s,2H).
example 7: synthesis of ethyl 4-aminobenzoate
To an isopropanol (3mL) solvent added with PtFeNPore (7.2mg,10 mol%) catalyst, the substrate ethyl 4-nitrobenzoate (105.11mg,0.5mmol) and hydrogen (3MPa) were added, the mixture was placed on a magnetic stirrer and reacted at 50 ℃ for 18h, and column chromatography (silica gel, 200 mesh 300; developing solvent, petroleum ether: ethyl acetate: 10: 1) was carried out to obtain 97.75mg of ethyl 4-nitrobenzoate with a yield of 93%.
Figure BDA0002660217550000071
A light yellow solid;1H NMR(400MHz,CDCl3):7.86(t,J＝5.5Hz,2H),6.63(d,J＝8.6Hz,2H),4.31(q,J＝7.1Hz,2H),1.36(t,J＝7.1Hz,3H).
example 8: synthesis of ethyl 4-aminobenzoate
To a solvent of PtFeNPore (3.6mg,5 mol%) in methanol (3mL) with catalyst, substrate 4-nitrobenzoic acid ethyl ester (105.11mg,0.5mmol) and hydrogen (0.1MPa) were added, the mixture was placed on a magnetic stirrer and reacted at 25 ℃ for 24h, and column chromatography (silica gel, 200-mesh 300; developing solvent, petroleum ether: ethyl acetate ═ 10: 1) was carried out to obtain 99.85mg of 4-nitrobenzoic acid ethyl ester with a yield of 95%.
Figure BDA0002660217550000072
A light yellow solid;1H NMR(400MHz,CDCl3):7.86(t,J＝5.5Hz,2H),6.63(d,J＝8.6Hz,2H),4.31(q,J＝7.1Hz,2H),1.36(t,J＝7.1Hz,3H).
example 9: synthesis of 4-bromoaniline
To a solvent of PtFeNPore (3.6mg,5 mol%) in methanol (3mL) with catalyst, substrate 4-bromonitrobenzene (101mg,0.5mmol) and hydrogen (0.2MPa) were added, and the mixture was reacted for 24h at 25 ℃ on a magnetic stirrer, and column chromatography (silica gel, 200 mesh, 300 mesh; developing solvent, petroleum ether: ethyl acetate ═ 10: 1) was carried out to obtain 81.7mg of 4-bromoaniline with a yield of 95%.
Figure BDA0002660217550000081
Light yellow solid:1H NMR(400MHz,CDCl3)7.41–7.08(m,2H),6.77–6.25(m,2H),3.65(s,2H).
example 10: synthesis of 4-bromoaniline
To an ethyl acetate (3mL) solvent added with PtFeNPore (7.2mg,10 mol%) catalyst, the substrate 4-bromonitrobenzene (101mg,0.5mmol) and hydrogen (0.5MPa) are added, the mixture is placed on a magnetic stirrer to react for 24h at 25 ℃, and column chromatography (silica gel, 200 meshes and 300 meshes; developing agent, petroleum ether: ethyl acetate: 10: 1) is carried out to obtain 80.9mg of 4-bromoaniline with the yield of 94%.
Figure BDA0002660217550000082
Light yellow solid:1H NMR(400MHz,CDCl3)7.41–7.08(m,2H),6.77–6.25(m,2H),3.65(s,2H).
example 11: synthesis of 4-bromoaniline
To a methanol (3mL) solvent added with PdNPore (2.7mg,5 mol%) catalyst, substrate 4-bromonitrobenzene (101mg,0.5mmol) and hydrogen (0.2MPa) are added, the mixture is placed on a magnetic stirrer to react for 24h at 25 ℃, and column chromatography (silica gel, 200 meshes and 300 meshes; developing solvent, petroleum ether and ethyl acetate: 10: 1) is carried out to obtain 12.9mg of 4-bromoaniline with 15% yield, and debromination reaction is carried out to obtain 37.3mg of aniline with 80% yield.
Figure BDA0002660217550000091
Light yellow solid:1H NMR(400MHz,CDCl3)7.41–7.08(m,2H),6.77–6.25(m,2H),3.65(s,2H).
Figure BDA0002660217550000092
a yellow-brown liquid;1H NMR(400MHz,CDCl3)7.59–7.13(m,2H),7.07–6.82(m,1H),6.82–6.46(m,2H),3.90–3.49(m,2H).
example 12: synthesis of 4-bromoaniline
To an ethyl acetate (3mL) solvent added with PdNPore (5.4mg,10 mol%) catalyst, substrate 4-bromonitrobenzene (101mg,0.5mmol) and hydrogen (0.5MPa) are added, the mixture is placed on a magnetic stirrer to react for 24h at 25 ℃, and column chromatography (silica gel, 200 meshes and 300 meshes; developing solvent, petroleum ether and ethyl acetate: 10: 1) is carried out to obtain 8.6mg of 4-bromoaniline with 10% yield, and debromination reaction is carried out to obtain 40.9mg of aniline with 88% yield.
Figure BDA0002660217550000093
Light yellow solid:1H NMR(400MHz,CDCl3)7.41–7.08(m,2H),6.77–6.25(m,2H),3.65(s,2H).
Figure BDA0002660217550000101
a yellow-brown liquid;1H NMR(400MHz,CDCl3)7.59–7.13(m,2H),7.07–6.82(m,1H),6.82–6.46(m,2H),3.90–3.49(m,2H).
example 13: synthesis of 4-bromoaniline
To a methanol (3mL) solvent added with 5% Pt/C (97.54mg,5 mol%) catalyst was added the substrate 4-bromonitrobenzene (101mg,0.5mmol), hydrogen (0.2MPa), placed on a magnetic stirrer and reacted at 25 ℃ for 24h, and column chromatography (silica gel, 200 mesh 300 mesh; developing solvent, petroleum ether: ethyl acetate: 10: 1) gave 4.3mg of 4-bromoaniline, yield 5%, debromination occurred to give 41.9mg of aniline, yield 90%.
Figure BDA0002660217550000102
Light yellow solid:1H NMR(400MHz,CDCl3)7.41–7.08(m,2H),6.77–6.25(m,2H),3.65(s,2H).
Figure BDA0002660217550000103
a yellow-brown liquid;1H NMR(400MHz,CDCl3)7.59–7.13(m,2H),7.07–6.82(m,1H),6.82–6.46(m,2H),3.90–3.49(m,2H).
example 14: synthesis of 4-bromoaniline
To an ethyl acetate (3mL) solvent to which 5% Pt/C (195.08mg,10 mol%) catalyst was added, 4-bromonitrobenzene (101mg,0.5mmol) as a substrate and hydrogen (0.5MPa) were added, and the mixture was reacted for 24 hours at 25 ℃ on a magnetic stirrer, and column chromatography (silica gel, 200 mesh 300; developing solvent, petroleum ether: ethyl acetate 10: 1) did not yield 4-bromoaniline, and debromination occurred to yield 44.2mg of aniline in 95% yield.
Figure BDA0002660217550000111
A yellow-brown liquid;1H NMR(400MHz,CDCl3)7.59–7.13(m,2H),7.07–6.82(m,1H),6.82–6.46(m,2H),3.90–3.49(m,2H).
in conclusion, when PtFeNPore is used as a catalyst, a reaction system has high chemical selectivity and can selectively reduce nitro groups, so that corresponding aromatic amine compounds are obtained, and other groups are remained in the original positions and are not changed. In the comparative examples of 11-14, commercial 5% Pt/C and PdNPore are respectively used as catalysts to catalyze the reaction of reducing 1-bromo-4-nitrobenzene to prepare 4-bromoaniline, but the two catalysts have low chemical selectivity, cannot identify the difference between nitro groups and bromine, and have serious debromination reaction, so that a large amount of byproduct aniline is obtained, and the yield of the target product, namely 4-bromoaniline, is extremely low. Therefore, PtFeNPore is a catalyst with wide application prospect.

Claims (3)

1. The preparation method of the arylamine compound is characterized by comprising the following steps:
aromatic nitro compound is used as raw material, nano porous platinum iron catalyst is used as catalyst, hydrogen is used as hydrogen source, and arylamine is prepared by selective hydrogenation in solvent, and the synthetic route is as follows:
Figure FDA0002660217540000011
the reaction temperature is 25-100 ℃, and the reaction time is 10-50 h;
R1selected from the group consisting of hydrogen, alkyl, methoxy, hydroxy, halogen, phenoxy, amino, carbethoxy and methylmercapto;
R2selected from the group consisting of hydrogen, alkyl, methoxy, hydroxy, halogen, phenoxy, amino, carbethoxy and methylmercapto;
R1and R2The same or different;
the nano porous platinum-iron catalyst has the pore size of 1-50 nm, and the molar ratio of the aromatic nitro compound to the nano porous platinum-iron catalyst is 1: 0.01-1: 0.5;
the pressure of the hydrogen is 0.1-20.0 MPa;
the molar concentration of the aromatic nitro compound in the solvent is 0.01-2 mmol/mL.
2. The preparation method of claim 1, wherein the nanoporous platinum-iron catalyst is obtained by performing electrochemical corrosion dealloying on Fe-Pt-B alloy; the Pt-Fe atomic ratio of the nano porous platinum iron is Pt100-XFeX，X＝10～60。
3. The method according to claim 1 or 2, wherein the solvent is methanol, toluene, cyclohexane, dichloromethane, dichloroethane, N-dimethylformamide, tert-butanol, dimethyl ether, ethyl acetate, ethylene glycol dimethyl ether, tetrahydrofuran, acetone or ethanol.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115521226A (en) * 2022-10-20 2022-12-27 大连理工大学 Method for synthesizing imine by catalyzing aromatic nitro compound and aldehyde through nano porous ruthenium iron one-pot method
CN115677568A (en) * 2022-10-27 2023-02-03 南京晓庄学院 One-step amination method of p-methylphenol
CN115677568B (en) * 2022-10-27 2024-04-19 南京晓庄学院 One-step amination method of p-methylphenol

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