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Method for preparing pranlukast key intermediate 3-amino-2-hydroxyacetophenone

A technology for hydroxyacetophenone and intermediates, applied in the field of preparation of 3-amino-2-hydroxyacetophenone, the key intermediate of pranlukast, can solve the problems of low yield and long synthesis route, and achieve The effect of high purity, novel synthetic route, and easy control

Active Publication Date: 2017-08-29
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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  • Method for preparing pranlukast key intermediate 3-amino-2-hydroxyacetophenone
  • Method for preparing pranlukast key intermediate 3-amino-2-hydroxyacetophenone
  • Method for preparing pranlukast key intermediate 3-amino-2-hydroxyacetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The first step: the preparation of 2-acetamidophenol

[0042] Take 2-aminophenol (109kg), dissolve it in 250kg of water, add acetic anhydride (110kg) dropwise under ice bath, after the dropwise addition, warm up to room temperature and react for 2h. After the reaction, filter to obtain 142kg of light yellow solid, collect The rate is 94%.

[0043] The second step: the preparation of 2-acetamido-4-bromophenol

[0044] Take 75kg of 2-acetaminophen, dissolve it in 200kg of dichloromethane, cool in an ice bath to 0°C, add 90kg of NBS in batches, then warm up to room temperature and react for 3 hours. During the reaction, solids are gradually precipitated. After the reaction, filter and filter The cake was washed with 500kg of water, and dried to obtain 104kg of yellow solid powder, with a yield of 91%.

[0045] Step 3: Preparation of 2-hydroxy-3-amino-5-bromoacetophenone

[0046]Get 114kg of 2-acetamido-4-bromophenol, dissolve it in 200kg of acetonitrile, add 10kg of ZnC...

Embodiment 2

[0050] The first step: the preparation of 2-acetamidophenol

[0051] Take 2-aminophenol (110kg), dissolve it in 255kg of water, add acetic anhydride (112kg) dropwise under ice bath, after the dropwise addition, warm up to room temperature and react for 2h. After the reaction, filter to obtain 145kg of light yellow solid, collect The rate is 94%.

[0052] The second step: the preparation of 2-acetamido-4-bromophenol

[0053] Take 78kg of 2-acetaminophen, dissolve it in 210kg of dichloromethane, cool it in an ice bath to 0°C, add 92kg of NBS in batches, then raise the temperature to room temperature and react for 3 hours. During the reaction, solids are gradually precipitated. After the reaction, filter and filter The cake was washed with 500kg of water, and dried to obtain 106kg of yellow solid powder, with a yield of 91%.

[0054] Step 3: Preparation of 2-hydroxy-3-amino-5-bromoacetophenone

[0055] Get 115kg of 2-acetamido-4-bromophenol, dissolve it in 210kg of acetonitril...

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Abstract

The invention provides a method for preparing a pranlukast key intermediate 3-amino-2-hydroxyacetophenone. The method takes 2-aminophenol as an initial raw material, 2-aminophenol and acetic anhydride are subjected to a synthesis reaction in water to obtain 2-acetaminophenol, then 2-acetamido-4-bromophenol is prepared by 2-ace-taminophenol and NBS under room temperature, 2-hydroxy-3-amino-5-bromoacetophenone is prepared by a Hoesch reaction, finally 2-hydroxy-3-amino-5-bromoacetophenone is dissolved in ethanol, and a Pd / C is added for catalytic hydrogenation and bromine removal to obtain the 3-amino-2-hydroxyacetophenone. The raw materials have the advantages of low cost, easy acquisition, diversified raw material selection, easy realization of production technology, and easy control, the purity of the final product is high, no dangerous process is generated, the equipment is simple, the synthesis route is novel, the synthesis route is short, the production power is increased, and production processing cost is reduced.

Description

technical field [0001] The invention relates to a preparation method of a key intermediate of pranlukast medicine for treating asthma, that is, a preparation method of 3-amino-2-hydroxyacetophenone, a key intermediate of prankast. 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 mater...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/22
CPCC07C221/00C07C231/02C07C231/12C07C225/22C07C233/25
Inventor 刘辉
Owner 上海微巨实业有限公司
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