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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 and high reaction temperature, and achieves easy Purification, good product purity, and simple reaction operation

Inactive Publication Date: 2006-02-15
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-butyrylaminophenol butyrate

[0027] Add 50g (0.46mol) of m-aminophenol, 128ml (0.92mol) of triethylamine, and 200ml of dichloroethane to a 500ml four-neck flask in turn, add 100ml (0.98mol) of butyryl chloride dropwise at room temperature, add it in 30 minutes, and reflux The reaction was carried out for 4 hours. Stop the reaction, 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 for 3 times, dry the organic layer with anhydrous sodium sulfate, and concentrate the organic layer , recovery of dichloroethane to obtain oily liquid 110g, yield 96.4%.

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

[0029] In a 500ml four-necked flask, add 94g (0.38mol) 3-butyrylaminophenol butyrate, 101g (0.76mol) AlCl 3 And dichlorobenzene (200ml), heated up to 140 degrees to react for 4 hours, cooled, slowly poured into 200ml...

Embodiment 2

[0037] 1) Preparation of 3-butyrylaminophenol butyrate

[0038] Add 50g (0.46mol) of m-aminophenol, 36.8g (0.92mol) of sodium hydroxide, and 200ml of ethyl acetate in sequence in a 500ml four-neck flask, add 154.8g (0.98mol) of butyrylic anhydride dropwise at room temperature, and complete the addition in 30 minutes , reacted under reflux for 4 hours. Stop the reaction, 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 for 3 times, dry the organic layer with anhydrous sodium sulfate, and concentrate the organic layer , and recover ethyl acetate to obtain 106 g of oily liquid with a yield of 92.9%.

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

[0040] In a 500ml four-necked flask, add 94g (0.38mol) 3-butyrylaminophenol butyrate, 101g (0.76mol) AlCl 3 and sodium chloride (20g), heated to 120°C for 4 hours, cooled to 90°C, slowly added 20...

Embodiment 3

[0048] 1) Preparation of 3-butyrylaminophenol butyrate

[0049] Add 50g (0.46mol) of m-aminophenol, 127g (0.92mol) of potassium carbonate, and 200ml of toluene into a 500ml four-neck flask in sequence, and add 100ml (0.98mol) of butyryl chloride dropwise at room temperature, complete the addition in 30 minutes, and react under reflux for 5 hours . Stop the reaction, cool down, 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 with water for 3 times, dry the organic layer with anhydrous sodium sulfate, concentrate the organic layer, and recover the toluene , to obtain 98 g of oily liquid, yield 85.9%.

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

[0051] In a 500ml four-necked flask, add 94g (0.38mol) 3-butyrylaminophenol butyrate, 101g (0.76mol) AlCl 3 and 1,2-dichloroethane (200ml), warming up to 75°C for 6 hours, cooling, slowly adding 200ml of hydrochloric acid a...

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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 the intermediate 3-benzyloxy-4-butylaniline hydrochloride of the non-antibiotic anticoccidial drug naphthaquinate. Background technique [0002] 3-benzyloxy-4-butylaniline hydrochloride (structural formula such as I) is the important intermediate of synthetic non-antibiotics anticoccidial drug naquinate (Nequinate, structural formula such as II), existing preparation method (world patent [0003] [0004] WO9857921, European patent EP994846) to synthesize 3-benzyloxy-4-butylaniline, the main steps include: the first step, using m-aminophenol as raw material, condensing with butyryl chloride under alkaline conditions to obtain 3-butyrylamide Phenol butyrate; second step, 3-butyrylaminophenol butyrate in anhydrous AlCl 3 Under the action of Fries rearrangement reaction, 2-butyryl-5-butyrylamide phenol is generated; in the third step, 2-butyryl-5-butyrylamide phenol is hydrogenated and reduced under th...

Claims

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Application Information

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