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Method for reducing aromatic nitro compounds into aromatic amine compounds

A technology of nitro compounds and aromatic amines, which is applied in the field of reducing aromatic nitro compounds to aromatic amine compounds, which can solve the problems of unrecyclable catalysts, low catalyst activity, troublesome post-processing, etc., and achieve recyclable activity , Low production cost, simple operation

Active Publication Date: 2020-03-13
SHAANXI NORMAL UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In summary, the reported systems for reducing nitro groups have the following disadvantages: Fe / HCl or Sn / HCl systems produce a lot of waste, and post-processing is troublesome; some systems require high-pressure hydrogen, which is not easy to operate; some systems require Use formic acid to release greenhouse gas carbon dioxide; some systems use more expensive hydrazine hydrate or NH3 BH3 as hydrogen source; and when using cheap isopropanol as hydrogen Source Time (RSC Adv., 2016, 6, 100532-100545; Inorg.Chem., 2007, 46, 5779-5786; Catal.Sci.Technol., 2013, 3, 3200-3206; New J.Chem., 2015 , 39,5360-5365; Chem.Eur.J.2011,17,14375-14379), the catalyst activity is not high (0.25mmol%-1mmol%), and the homogeneous system cannot recycle the catalyst

Method used

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  • Method for reducing aromatic nitro compounds into aromatic amine compounds
  • Method for reducing aromatic nitro compounds into aromatic amine compounds
  • Method for reducing aromatic nitro compounds into aromatic amine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Under argon protection, add 123mg (1mmol) of nitrobenzene, 21.2mg (0.1mmol) of potassium phosphate, 1.37mg (0.0025mmol) of catalyst 1a, 1.53mL (20mmol) of isopropanol, and 1mL of water into a thick-walled pressure-resistant tube In the process, after stirring and reacting at 120°C for 10 minutes, the yield of aniline detected by gas chromatography was 85%; the reaction was continued to stir and react at 120°C for 3 hours (the yield of aniline detected by gas chromatography was 96%), cooled to room temperature, Extract with diethyl ether (5×3mL), dry the organic phase with anhydrous sodium sulfate, distill off the diethyl ether under reduced pressure to obtain aniline with a yield of 82%, and the characteristic data are: 1 H NMR (CDCl 3 ,400MHz)δ(ppm):7.21-7.16(m,2H),6.81-6.77(m,1H),6.72-6.70(m,2H),3.54(s,2H); 13 C NMR (CDCl 3 ,100MHz)δ(ppm):146.4,129.2,118.4,115.0; MS(EI)C 6 h 7 N[M] + :93.

Embodiment 2

[0019] Under the protection of argon, 153mg (1mmol) 4-nitromethyl sulfide, 21.2mg (0.1mmol) potassium phosphate, 5.48mg (0.01mmol) catalyst 1a, 1.53mL (20mmol) isopropanol, 1mL water were added to thick In a pressure-resistant tube with a wall, the reaction was stirred at 120°C for 24 hours, cooled to room temperature, extracted with ethyl acetate (5×3 mL), the organic phase was dried over anhydrous sodium sulfate, and the ethyl acetate was distilled off under reduced pressure to obtain 4-methoxy Base aniline, its productive rate is 97%, and characteristic data is: 1 H NMR (CDCl 3 ,400MHz)δ(ppm):7.75(d,J=8.8Hz,2H),6.65(d,J=9.2Hz,2H),3.75(s,3H),3.41(s,2H); 13 C NMR (CDCl 3 ,100MHz)δ(ppm):152.8,140.1,116.4,114.9,55.7; MS(EI)C 7 h 9 NO[M] + :123.

Embodiment 3

[0021] Under argon protection, add 169mg (1mmol) 4-nitroanisole, 21.2mg (0.1mmol) potassium phosphate, 9.73mg (0.02mmol) catalyst 1j, 1.53mL (20mmol) isopropanol, 1mL water into thick In a wall pressure tube, stir and react at 120°C for 24 hours, cool to room temperature, extract with ethyl acetate (5×3mL), dry the organic phase with anhydrous sodium sulfate, distill off ethyl acetate under reduced pressure to obtain 4-amino anise Thioether, its productive rate is 95%, and characteristic data is: 1 H NMR (CDCl 3 ,400MHz)δ(ppm):7.18(d,J=8.4Hz,2H),6.63(d,J=8.4Hz,2H),3.66(s,2H),2.41(s,2H); 13 C NMR (CDCl 3 ,100MHz)δ(ppm):145.1,130.9,125.5,115.7,18.6; MS(EI)C 7 h 9 NS[M] + :139.

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Abstract

The invention discloses a method for reducing aromatic nitro compounds into aromatic amine compounds. The aromatic nitro compounds are reacted at a temperature of 110-130 DEG C in an inert or air atmosphere under the action of a rhodium catalyst by using water as a solvent, isopropanol as a hydrogen source and potassium phosphate or sodium carbonate as an alkali to obtain the aromatic amine compounds. The method has the advantages of simplicity in operation, greenness, environmental friendliness, reduction of environmental pollution, high reaction yield, amplified gram-scale preparation of theamine compounds, high catalyst activity, recyclability and low industrial production cost.

Description

technical field [0001] The invention belongs to the technical field of nitro group reduction, and in particular relates to a method for reducing aromatic nitro compounds into aromatic amine compounds. Background technique [0002] Aromatic amines are important intermediates in dye synthesis, cosmetics, rubber chemicals, pharmaceuticals and agrochemicals. Aromatic amine compounds are mainly obtained by reduction of aromatic nitro compounds. There are many systems for the reduction of aromatic nitro compounds, mainly including: (1) The traditional Fe / HCl or Sn / HCl system can obtain the product of nitro group reduction to amino group. (2) Professor Matthias Beller's research group (J.Am.Chem.Soc.2011,133,12875–12879) reported in 2011 that Fe(BF 4 ) 2 ·6H 2 O as a catalyst, [P(CH 2 CH 2 PPh 2 ) 3 As a phosphorus ligand, formic acid is used as a hydrogen source, and at 40°C and ethanol as a solvent, a product in which a nitro group is reduced to an amino group can be obta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/36C07C211/46C07C213/02C07C217/84C07C211/55C07C211/47C07C253/30C07C255/58C07D295/135C07C215/76C07C319/20C07C323/36
CPCC07C209/36C07C213/02C07C253/30C07C319/20C07D295/135C07C211/46C07C211/55C07C211/47C07C217/84C07C255/58C07C215/76C07C323/36Y02P20/584
Inventor 王超刘宇轩李昌志肖建良张涛薛东汤卫军
Owner SHAANXI NORMAL UNIV
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