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Novel preparation method of 3-amino-2-hydroxyacetophenone

A technology of hydroxyacetophenone and a new method, which is applied in the field of preparation of 3-amino-2-hydroxyacetophenone, can solve the problems of long synthetic route and low yield, and achieve novel synthetic route, high purity and low The effect of processing costs on production

Inactive Publication Date: 2017-08-01
上海微巨实业有限公司
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  • Summary
  • 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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  • Novel preparation method of 3-amino-2-hydroxyacetophenone
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  • Novel preparation method of 3-amino-2-hydroxyacetophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0031] The first step: the preparation of 2-acetamidophenol acetate

[0032] Get 2-aminophenol (109kg), acetic anhydride (224kg), methanol 400kg, concentrated sulfuric acid 10 liters, reflux reaction 4h. After the reaction is finished, the methanol is recovered under reduced pressure, cooled to room temperature, and saturated sodium bicarbonate solution is added to the reaction system Adjusted to pH 9-10, extracted with 400 kg of ethyl acetate, washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the solvent was recovered under reduced pressure to obtain 191 kg of pale yellow solid with a yield of 99%.

[0033] The second step: the synthesis of 3-amino-2-hydroxyacetophenone

[0034] Take 96 kg of 2-acetamidophenol acetate, dissolve it in 250 kg of N-methylpyrrolidone, add 94 kg of anhydrous titanium tetrachloride, and react at 120 degrees for 3 h. After the reaction, most of the solvent is recovered under reduced pressure, and cooled to room temp...

Embodiment 2

[0036] The first step: the preparation of 2-acetamidophenol acetate

[0037] Get 2-aminophenol (110kg), acetic anhydride (225kg), methanol 410kg, concentrated sulfuric acid 11 liters, backflow reaction 4h. After the reaction, the methanol was recovered under reduced pressure, cooled to room temperature, and saturated sodium bicarbonate solution was added to the reaction system Adjusted to pH 9-10, extracted with 410 kg of ethyl acetate, washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the solvent was recovered under reduced pressure to obtain 191.5 kg of light yellow solid with a yield of 99.1%.

[0038] The second step: the synthesis of 3-amino-2-hydroxyacetophenone

[0039] Take 95kg of 2-acetamidophenol acetate, dissolve it in 245kg of N-methylpyrrolidone, add 93kg of anhydrous titanium tetrachloride, and react at 120 degrees for 3h. After the reaction, most of the solvent is recovered under reduced pressure and cooled to room temperature....

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Abstract

The invention provides a novel preparation method of 3-amino-2-hydroxyacetophenone. The novel preparation method comprises the following steps of using 2-aminophenol as an initial raw material; enabling the 2-aminophenol and acetic anhydride to synthesize 2-acetamidophenol acetate in a polar solvent under the alkaline or acid catalyzing condition; then, performing Fries rearrangement on the 2-acetamidophenol acetate in an aprotic solvent under the catalyzing action of anhydrous titanium tetrachloride, and adopting an acid hydrolysis one-pot method, so as to synthesize the 3-amino-2-hydroxyacetophenone. The novel preparation method has the advantages that the price of the used raw materials is low, the obtaining is easy, and the selection of the raw materials is diversified; the implementing of the production technology is easy, the management and control are easy, the purity of a final product is high, the dangerous technology is avoided, the equipment is simple, the synthesizing route is novel and short, the production capacity is increased, and the production and processing cost is reduced.

Description

technical field [0001] The invention relates to a preparation method of a key intermediate of a drug for treating asthma, prankast, in particular to a new preparation method of 3-amino-2-hydroxyacetophenone. Background technique [0002] Pranlukast (pranlukast, 1), 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 listed in Japan in 1995 and is mainly used as an anti-asthma and anti-allergic drug in clinical practice. It has good curative effect on the prevention and treatment of otitis media, dysmenorrhea and psoriasis, etc. At the same time, it can obviously improve the cerebral ischemia of animals, and has mild adverse reactions to the central nervous system. [0003] 3-Amino-2-hydroxyacetophenone is used as the key intermediate of pranlast, and its synthesis method mainly has the following two kinds: one kind of scheme is to take p-bromophe...

Claims

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Application Information

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IPC IPC(8): C07C45/54C07C49/825
CPCC07C45/54C07C231/14C07C49/825C07C233/25
Inventor 刘辉
Owner 上海微巨实业有限公司
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