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New preparation method of 3-amino-2-hydroxyphenylacetone

A technology of hydroxyacetophenone and a new method, applied in the field of medicine, can solve the problems of low yield, long synthetic route and the like, and achieve the effects of high purity, simple equipment and easy availability

Active Publication Date: 2017-06-13
上海微巨实业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic route is long, the reduction requires high-pressure hydrogenation, and the yield is low

Method used

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  • New preparation method of 3-amino-2-hydroxyphenylacetone
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  • New preparation method of 3-amino-2-hydroxyphenylacetone

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Embodiment 1: the preparation (I) of 3-acetamido-4-acetoxybenzenesulfonic acid

[0023] Take 2-aminophenol-4-sulfonic acid (189g), acetic anhydride (224g), methanol 400g, concentrated sulfuric acid 10ml, reflux reaction for 4h. After the reaction, recover methanol under reduced pressure, cool to room temperature, add The saturated sodium bicarbonate solution was adjusted to pH 9-10, extracted with 400 ml of ethyl acetate, washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the solvent was recovered under reduced pressure to obtain 264 g of light yellow solid with a yield of 97%.

Embodiment 2

[0024] Example 2: Synthesis of 3-amino-2-hydroxyacetophenone (II)

[0025] Take 136g of 3-acetamido-4-acetoxybenzenesulfonic acid, dissolve it in 300ml of chloroform, add 133g of anhydrous aluminum trichloride, and heat to reflux for 5h. After the reaction is over, recover most of the solvent under reduced pressure and cool to At room temperature, under an ice bath, the reaction solution was slowly added to 30% dilute hydrochloric acid, stirred at room temperature for 2 hours, slowly raised to reflux, and reacted for 4 hours. After the reaction, the reaction solution was cooled to room temperature, and 20% sodium hydroxide solution was added to the reaction system Adjust pH9-10. Add 300 ml of chloroform for extraction, wash with water until neutral, dry over anhydrous sodium sulfate, filter, and recover the filtrate under reduced pressure. The residue is recrystallized with petroleum ether: ethyl acetate = 1:3 to obtain 65.7 g of a light yellow solid, with a yield of 87%.

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Abstract

The invention discloses a new preparation method of a key intermediate, namely 3-amino-2-hydroxyphenylacetone, for preparation of Pranlukast. The new preparation method comprises the following main steps: taking 2-aminophenol-4-sulfonic acid as a starting raw material, and carrying out acylation, Fries rearrangement, hydrolysis and deprotection, so that 3-amino-2-hydroxyphenylacetone is obtained. Compared with the prior art, the new preparation method disclosed by the invention has the advantages that the used raw materials are cheap and easily available, technology can easily realize industrialization, and the obtained final product is high in purity; no danger technology is adopted, and equipment is simple; and route is novel, and synthesis route is short.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a new preparation method of 3-amino-2-hydroxyacetophenone. Background technique [0002] Pranlukast (pranlukast, 1), the chemical name is N-[4-oxo-2-(1H-tetrazol-5-yl)-4H-1-benzopyran-8-yl]-4- (4-Phenylbutoxy)benzamide is a leukotriene receptor antagonist developed by Japan's Ono Company. It was first launched in Japan in 1995 and is mainly used clinically as an anti-asthma and anti-allergy drug. It has a good curative effect on the prevention and treatment of otitis media, dysmenorrhea and psoriasis; meanwhile, it can obviously improve the cerebral ischemia in animals, and has mild adverse reactions to the central nervous system. [0003] 3-amino-2-hydroxyacetophenone is the key intermediate of pranlukast, and its synthetic method mainly contains following two kinds: one kind of scheme is to be raw material with p-bromophenol, through acylation, Fries rearrangement, nitration, Made by ...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/22
CPCC07C221/00C07C303/22C07C225/22C07C309/51
Inventor 刘辉
Owner 上海微巨实业有限公司
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