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Method for producing N-alkyl-(3,4-methylenedioxy) aniline

A methylene dioxy, alkyl technology, applied in the field of N-alkyl-aniline, can solve problems such as complicated operation, achieve the effects of good selectivity, less environmental pollution, and lower production costs

Inactive Publication Date: 2008-08-20
WUXUE LONGXIANG MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the alkylation reaction still needs to be carried out under the condition of hydrogen and pressure, and an additional alkylating agent is required, so the operation is still cumbersome

Method used

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  • Method for producing N-alkyl-(3,4-methylenedioxy) aniline
  • Method for producing N-alkyl-(3,4-methylenedioxy) aniline

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[0013] Example 1. Take 125g of 3,4-(methylenedioxy)nitrobenzene, 25g of Raney nickel catalyst, and 275g of dehydrated ethanol and put them into an autoclave, feed hydrogen, and react at 80°C / 2.5MPa for 2 hours. Replaced with nitrogen, raised the temperature to 170°C, and reacted for 10 hours. The product was concentrated and distilled under high vacuum, and 115g of fractions between 130-150°C were collected, analyzed by gas chromatography, the content of N-ethyl-(3,4-methylenedioxy)aniline was 96.4%, and the yield was 93.1% . 3,4-methylenedioxyaniline was not detected.

[0014] Example 2, 125g of 3,4-(methylenedioxy)nitrobenzene, 25g of Raney catalyst, and 275g of methanol were mixed and put into an autoclave, and hydrogen was passed through to react at 70°C / 2.5MPa for 2.5 hours. Replaced with nitrogen, raised the temperature to 160°C, and reacted for 10 hours. The product was concentrated and distilled under high vacuum, and 106g of fractions between 125-145°C were collecte...

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Abstract

A preparation method of N-alkyl-(3, 4-methylenedioxy) aniline relates to the method of the N-alkyl-(3, 4-methylenedioxy) aniline. 3, 4-(methylenedioxy) nitrobenzene in a pressure kettle is taken as the starting raw material, C1 to C4 lower aliphatic alcohols are taken as reaction solvents and alkylation reagents, a reductive alkylation catalyst is added, the pressure kettle is sealed, hydrogen gas is introduced for replacement, the temperature is increased, the hydrogen is introduced, the hydrogenation reaction is finished, the temperature is decreased, the pressure is relieved, then the N-alkylation reaction, the nitrogen introducing for replacement and the temperature increase reaction are continuously carried out for preparing the N-alkyl-(3, 4-methylenedioxy) aniline. In the preparation method, the hydrogenation reduction and the N-alkylation reaction are carried out in a same reaction kettle, the reduction products do not need to be separated, aldehyde and ketone alkylation reagents do not need to be added, and the N-alkylation reaction is directly carried out. The preparation method has small environmental pollution, good N-alkylation selectivity and high conversion rate, the raw material is easy to be recovered, the catalyst can be applied, the production cost is low, and the production process can be simplified.

Description

technical field [0001] The present invention relates to a process for N-alkyl-(3,4-methylenedioxy)anilines. Background technique [0002] At present, there are mainly two methods for synthesizing N-alkyl-(3,4-methylenedioxy)aniline both at home and abroad: one is as described in European Patent EP0549263, using 3,4-methylenedioxybenzene and Bromination with hydrobromic acid, followed by ammoniation reaction with ammonia water in an autoclave to obtain N-ethyl-(3,4-methylenedioxy)aniline. This method has the disadvantages of "three wastes" pollution, troublesome post-treatment, difficult separation of target products, low yield, and difficult recovery of raw materials. Hydrobromic acid is easy to corrode equipment, and alkane ammonolysis requires high temperature and pressure, so the requirements for equipment are very high. [0003] The other is the hydrogenation reduction method, generally 3,4-(methylenedioxy)nitrobenzene is first hydrogenated and reduced under the cataly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/66
Inventor 赵勇王存亮黄桂泉
Owner WUXUE LONGXIANG MEDICINE
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