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Chemical synthesizing method for 5-chlorine-2-nitroaniline

A technology for nitroaniline and synthesis method, applied in chemical instruments and methods, preparation of amino compounds, organic chemistry, etc., can solve the problems of long reaction time and high cost, and achieve high selectivity, convenient processing and small steric hindrance Effect

Inactive Publication Date: 2003-05-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses acetic anhydride as a protecting group, and the cost is relatively high; when 3-chloroacetanilide is nitrated, in addition to generating 5-chloro-2-nitroacetanilide, a certain proportion of by-product 3-chloro-4-nitro Acetanilide: 5-chloro-2-nitroacetanilide is prepared by alcoholysis with sodium methoxide / methanol solution to prepare 5-chloro-2-nitroaniline. The reaction time is very long and the cost is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 3-Chloroformanilide: In a 250ml three-necked flask equipped with a water separator, add 51.5g (0.41mol) 3-chloroaniline and 150ml toluene, stir to dissolve, then slowly add 23.5g (0.45mol) 88% formic acid , heat up and reflux for 1h, cool to 65-70°C, add 6.4g (0.12mol) 88% formic acid, heat up and reflux again for 1h, cool to room temperature, remove toluene and excess formic acid on a rotary evaporator, cool to obtain white Solid 3-chloroformanilide 61.7g, yield 97%, m.p.51~53℃.

Embodiment 2

[0017] 3-Chloroformanilide: except that benzene was used instead of toluene, other operating conditions were the same as in Example 1 to obtain 53.8 g of 3-chloroformanilide as a white solid with a yield of 84%, m.p.50-53°C.

Embodiment 3

[0019] 3-Chloroformanilide: except that n-butyl ether was used instead of toluene, other operating conditions were the same as in Example 1 to obtain 58.2 g of 3-chloroformanilide as a white solid, yield 91%, m.p.51-53°C.

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PUM

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Abstract

The method for synthesizing 5-chloro-2-nitrophenylamine uses 3-chlorophenylamine as initial raw material, and utilizes three-step reaction of formylation, nitration and hydrolysis to synthesize object compound 5-chloro-2-nitrophenylamine, its total yield rate is above 60% and its product purity is above 98%.

Description

Technical field: [0001] The present invention relates to a new method for synthesizing 5-chloro-2-nitroaniline. The method uses 3-chloroaniline as a starting material to synthesize target compound 5-chloro-2-nitroaniline through three steps of formylation, nitration and hydrolysis. Background technique: [0002] 5-Chloro-2-nitroaniline is an important pharmaceutical and pesticide intermediate. The method for the preparation of 5-chloro-2-nitroaniline reported in the literature is to take 3-chloroaniline as starting material, first reacts with acetic anhydride to prepare 3-chloroacetanilide, then in the mixed solvent of acetic acid and acetic anhydride, use Nitration with fuming nitric acid produced 5-chloro-2-nitroacetanilide, and finally reflux reaction in sodium methoxide / methanol solution for 24 hours to synthesize the target compound 5-chloro-2-nitroacetaniline (GB2018766). This method uses acetic anhydride as a protecting group, and the cost is relatively high; when 3...

Claims

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Application Information

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IPC IPC(8): C07C209/76C07C211/52
Inventor 杜晓华徐振元俞锋马肖克
Owner ZHEJIANG UNIV OF TECH
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