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Synthesis of nitroarylamine compound

A technology of nitroarylamines and compounds, which is applied in the field of synthesis of nitroarylamines, and achieves the effects of large-scale industrial production, good reduction selectivity, and low equipment investment

Inactive Publication Date: 2003-03-19
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Selenium-Catalyzed Reduction of Aromatic Nitro Compounds to Amines by CO / H2O in the Selenium-Catalyzed Reduction of Aromatic Nitro Compounds to Amines has been reported (T Miyata, K Kondo, S Murai, T Hirashima and N Sonoda. Presence of Triethylamine.Angew Chem Int EdEngl, 1980, 19(12): 1008), the yield is moderate to good, but triethylamine must be used as a cocatalyst

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add m-dinitrobenzene (10mmol), Se (0.2mmol), H 2 O (0.5mol), sodium acetate (20mmol) and solvent DMF (40ml), continue to feed carbon monoxide, and heat to 88 ° C and stir for 4 hours, cool to room temperature, switch carbon monoxide to oxygen or air and stir for 0.5-1 hour , filter out the selenium powder, concentrate the filtrate obtained by filtering, and separate it with a chromatographic column to obtain m-nitroaniline. The separation yield is 95% (calculated as m-dinitrobenzene).

Embodiment 2

[0025] The aromatic dinitro substance is p-dinitrobenzene, and other experimental methods and conditions are the same as in Example 1. The yield of p-nitroaniline obtained by column separation is 89% (calculated as p-dinitrobenzene).

Embodiment 3

[0027] Aromatic dinitro is 2,6-dinitrotoluene, and the reaction time is 4 hours, and other experimental methods and conditions are the same as in Example 1, and the column separation to obtain 2-methyl-4-nitroaniline yield is 98% (with 2,6-Dinitrotoluene).

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Abstract

Nitroarylamine compound is prepared with aromatic dinitro compound and through single nitro selecting reduction reaction in organic solvent at normal pressure in the presence of CO and water by using Se as catalyst and alkali as cocatalyst. The said aromatic dinitro compound may have substituent radical in the phenyl radical and the substituent radical may be one or several eletron donating and / or accepting group. The reaction conditions includes the molar ratio between aromatic dinitro compound and water of 1 to 1-1000; molar amount of Se is 0.1-100 % of the aromatic dinitro compound; molar amount of alkali is 0-400 % of the aromatic dinitro compound; the weight ratio between aromatic dinitro compound and solvent of 1 to 2-1000; reaction time of 1-36 hr; and reaction temperature of 20-120 deg.c.

Description

technical field [0001] The invention relates to a method for synthesizing nitroarylamine compounds, in particular to a method for synthesizing nitroarylamine compounds through selenium-catalyzed single nitro group selective reduction under normal pressure using carbon monoxide and water. Background technique [0002] As a large class of important organic synthesis intermediates and raw materials, nitroarylamines are widely used in medicine, pesticides, dyes and other fields. At present, the selective reduction of aromatic dinitro compounds is an important method for preparing nitroarylamines, but there are not many methods. In general, the selective reduction methods of dinitro compounds used in industrialization mainly include the following: iron filings reduction, alkali sulfide reduction, and tin chloride reduction. Iron filings method and soda sulfide method have wide adaptability, simple process, and high reduction conversion rate, but serious environmental pollution, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/36C07C211/52
Inventor 刘晓智陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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