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3-benzyloxy-4-butylaniline hydrochloride preparation method

A technology of butylaniline and butyrylaniline, which is applied in the field of preparation of 3-benzyloxy-4-butylaniline hydrochloride, can solve the problems of difficult separation and purification, difficult complete reaction, long reaction time and the like, and achieves The effect of easy purification, good product purity and simple reaction operation

Inactive Publication Date: 2008-10-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The disadvantage of this method is that no solvent or co-solvent is used in the third step reaction, resulting in high reaction temperature, difficult stirring, and difficult reaction to complete; in the fourth step reaction, expensive palladium carbon catalyst is used, and the reaction time is long and the efficiency is low ;The final product is an oily liquid, not easy to separate and purify, and unstable

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0026] 1) Preparation of 3-butyramidophenol butyrate

[0027] In a 500ml four-necked flask, add 50g (0.46mol) of m-aminophenol, 128ml (0.92mol) of triethylamine, and 200ml of dichloroethane. Add 100ml (0.98mol) of butyryl chloride dropwise at room temperature. After 30 minutes, reflux React for 4 hours. Stop the reaction, cool down, filter with suction, and rinse the filter cake with 100ml of dichloroethane; then pour the filtrate into a 1L separatory funnel, add 400ml of water, wash 3 times with water, dry the organic layer with anhydrous sodium sulfate, and concentrate the organic layer , Recovery of dichloroethane, 110g of oily liquid, yield 96.4%.

[0028] 2) Preparation of 2-butyryl-5-butyramidophenol

[0029] Add 94g (0.38mol) 3-butamidophenol butyrate and 101g (0.76mol) AlCl into a 500ml four-necked flask 3 React with dichlorobenzene (200ml) at 140°C for 4 hours, cool, slowly pour 200ml hydrochloric acid and 400ml ice water with rapid stirring, keep the mixture at low tempe...

Embodiment 2

[0037] 1) Preparation of 3-butyramidophenol butyrate

[0038] In a 500ml four-necked flask, add 50g (0.46mol) of m-aminophenol, 36.8g (0.92mol) of sodium hydroxide, and 200ml of ethyl acetate. Add 154.8g (0.98mol) of butyryl anhydride dropwise at room temperature, and finish in 30 minutes. , React under reflux for 4 hours. After the reaction is stopped, cool slightly, filter with suction, and rinse the filter cake with 100ml of dichloroethane; then pour the filtrate into a 1L separatory funnel, add 400ml of water, wash with water three times, dry the organic layer with anhydrous sodium sulfate, and concentrate the organic layer , The ethyl acetate was recovered to obtain 106 g of oily liquid with a yield of 92.9%.

[0039] 2) Preparation of 2-butyryl-5-butyramidophenol

[0040] Add 94g (0.38mol) 3-butamidophenol butyrate and 101g (0.76mol) AlCl into a 500ml four-necked flask 3 React with sodium chloride (20g) at 120°C for 4 hours, then cool to 90°C, slowly add 200ml hydrochloric ac...

Embodiment 3

[0048] 1) Preparation of 3-butyramidophenol butyrate

[0049] Add 50g (0.46mol) m-aminophenol, 127g (0.92mol) potassium carbonate, and 200ml toluene in a 500ml four-necked flask. Add 100ml (0.98mol) of butyryl chloride dropwise at room temperature. After 30 minutes, add it and react for 5 hours under reflux. . After the reaction is stopped, cool slightly, filter with suction, and rinse the filter cake with 100ml of toluene; then pour the filtrate into a 1L separatory funnel, add 400ml of water, wash 3 times in succession, dry the organic layer with anhydrous sodium sulfate, concentrate the organic layer, and recover the toluene , 98 g of oily liquid was obtained, and the yield was 85.9%.

[0050] 2) Preparation of 2-butyryl-5-butyramidophenol

[0051] Add 94g (0.38mol) 3-butamidophenol butyrate and 101g (0.76mol) AlCl into a 500ml four-necked flask 3 And 1,2-dichloroethane (200ml), warm up to 75 degrees and react for 6 hours, cool, slowly add 200ml hydrochloric acid and 400ml ice-...

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Abstract

The invention provides a process for preparing 3-benzyloxy-4-butylaniline hydrochlorides, which comprises using m-aminophenol as raw material, carrying out butanoylation reaction and Fries rearrangement, obtaining 2-butyryl-5-butyramidophenol, under the action of alkali, reacting 2-butyryl-5-butyramidophenol with benzyl halides, obtaining 2-butyryl-5-butyramidophenyl benzyl ether, hydrolyzing to obtain 3-benzyloxy-4-butyryl benzeneamine, finally carrying out Huangminglong reduction reaction to obtain 3-benzyloxy-4-butylaniline hydrochlorides.

Description

Technical field [0001] The invention relates to a preparation method of 3-benzyloxy-4-butylaniline hydrochloride, an intermediate of the non-antibiotic anticoccidial drug naphthoquinate. Background technique [0002] 3-benzyloxy-4-butylaniline hydrochloride (structure like I) is an important intermediate for the synthesis of non-antibiotic anticoccidial drugs Nequinate (structure like II). The existing preparation method (World patent [0003] [0004] WO9857921, European Patent EP994846) synthesize to obtain 3-benzyloxy-4-butylaniline. The main steps include: the first step is to use m-aminophenol as a raw material and condense with butyryl chloride under alkaline conditions to obtain 3-butyramide. Phenol butyrate; The second step, 3-butamidophenol butyrate is in anhydrous AlCl 3 The Fries rearrangement reaction occurs under the action to produce 2-butyryl-5-butyramidophenol; in the third step, 2-butyryl-5-butyramidophenol is hydrogenated and reduced under Pd / C catalysis to ob...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/86C07C213/08
Inventor 王晓钟张世界戴立言陈英奇
Owner ZHEJIANG UNIV