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Method for preparing Adapalene

An equation and reaction technology, applied in the preparation of carboxylate/lactone, organic chemistry, etc., can solve the problems of three wastes, high cost, difficult industrial production, etc., and achieve the effects of reducing three wastes, easy operation and improving yield

Inactive Publication Date: 2006-12-06
JIANGSU ZHONGDAN GROUP +2
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Problems solved by technology

Document US4717720 reports the laboratory synthesis of adapalene, using p-bromophenol as a raw material, through four steps of substitution, methylation, coupling and hydrolysis to obtain the product, the yield is 36.95%, industrial production is difficult, and the cost is high, three waste serious

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  • Method for preparing Adapalene

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Embodiment Construction

[0013] Preparation of 2-(1-adamantyl)-4-bromoanisole

[0014] Add 14.02g of p-bromoanisole, 11.4g of 1-adamantol and 250ml of dichloromethane into a 500ml reactor, stir and dissolve, add 3.75ml of concentrated sulfuric acid dropwise at room temperature, and react at room temperature for 8 hours. The reaction mixture was poured into 250ml of water, allowed to stand to separate layers, and the dichloromethane layer was washed three times with 20ml of saturated sodium bicarbonate solution, and then washed with water until neutral. The lower organic phase was separated and concentrated under reduced pressure to obtain a crude product. The crude product was dissolved with an appropriate amount of petroleum ether, filtered through silica gel, washed with an appropriate amount of petroleum ether, and the eluent was vacuum-precipitated to obtain 18.3 g of a white solid with a yield of 76.1% and a melting point of 136-137°C.

[0015] Preparation of methyl 6-[3-(1-adamantyl)-4-methoxyph...

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Abstract

This invention discloses a method for preparing adapalene. The method comprises: (1) reacting halogenated anisole and adamantanol in solvent in the presence of acid at -10-150 deg.C to obtain 2-(1-adamantyl)-4-bromophenyl ether; (2) reacting with magnesium in the presence of iodine, iodide or bromide in ether or a nonpolar solvent to obtain a Grignard reagent; (3) reacting with 6-bromo-2-naphthoate, and hydrolyzing with a base to obtain adapalene. The method has such advantages as high product yield, few side reactions, simple operation, little pollution and low cost, and is suitable for mass production.

Description

technical field [0001] The invention relates to a method for preparing adapalene from p-halogen anisole as a starting material. Background technique [0002] Adapalene (adapalene), chemical name 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid, is an aryl propionic acid derivative, a new naphthalene Formic acid derivatives, belonging to the third generation of retinoic acid drugs, are selective β-retinoic acid receptor agonists, and are clinically used to treat acne and psoriasis. Document US4717720 reports the laboratory synthesis of adapalene, using p-bromophenol as a raw material, through four steps of substitution, methylation, coupling and hydrolysis to obtain the product, the yield is 36.95%, industrial production is difficult, and the cost is high, three waste serious. [0003] Contents of the invention [0004] In order to solve the above problems, the present invention provides a method for preparing adapalene. [0005] Preparation method of the present ...

Claims

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Application Information

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IPC IPC(8): C07C51/09C07C65/26
Inventor 张家庆陈捷周春红翟富荣周玉琢龚熙见
Owner JIANGSU ZHONGDAN GROUP
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