Method for preparing 2-acetamido-6-acetylphenol

An acetone-based phenol and acetamido-based technology is applied in the field of preparing 2-acetamido-6-ethanone-based phenol, can solve the problems of high cost, large pollution, long route and the like, and achieves low cost, low pollution, The effect of a wide range of raw materials

Inactive Publication Date: 2011-05-18
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The existing main synthesis route of 2-acetamido-6-ethanone phenol is: using p-hydroxyphenol as raw material, the final product can only be obtained after acetylation, rearrangement, nitration, debromination and acylation, and there is a route Long, high cost, large pollution and other disadvantages

Method used

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  • Method for preparing 2-acetamido-6-acetylphenol
  • Method for preparing 2-acetamido-6-acetylphenol
  • Method for preparing 2-acetamido-6-acetylphenol

Examples

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Effect test

Embodiment 1

[0022] Step 1, preparation of intermediate I: (2-acetamido-4-chloro)phenyl acetate

[0023] Add 24.0g of 2-amino-4-chlorophenol (0.168mol) and 88.0g of ethyl acetate into a 250mL three-necked flask, slowly add 15.1g of acetyl chloride (0.420mol) dropwise in a water bath, and drop it for about 1 hour. Then, the temperature was raised to 70° C. and kept under reflux for 2 hours, and then 21.0 g of triethylamine (0.208 mol) was slowly added dropwise. At this time, the pH of the solution was neutral. After about 0.5 hours of dropping, the mixture was continued to keep stirring for 15 minutes. TLC detects that the raw material point disappears, and there is only one point of the product. The reaction solution was cooled to 10°C and then filtered. The filtrate can be applied directly for the next use. Add the filter cake and 120mL water into a 250L reaction flask, stir at 40°C for 1 hour, then filter, wash the filter cake 3 times with water (5mL*3), and then dry the product to obt...

Embodiment 2

[0042] Embodiment 2 Pilot test scheme

[0043] Step 1, preparation of intermediate I: (2-acetamido-4-chloro)phenyl acetate

[0044] Add 24.0kg of 2-amino-4-chlorophenol (0.168kmol), 34.0kg of triethylamine (0.336kmol) and 88kg of ethyl acetate into a 200L reactor, and slowly add 15.1kg of acetyl chloride (0.420kmol) dropwise at room temperature , and then heated to 70 ° C to maintain a slight reflux reaction for 4h. The reaction solution was cooled to 10°C and then centrifuged. The filtrate can be applied directly for the next use. Add the filter cake and 120kg of water into a 200L reactor, stir at 40°C for 1 hour, centrifuge, wash the filter cake with water 3 times (5L*3), and then dry the product to obtain 34.2kg of the product, with a yield of 90%.

[0045] Step 2, preparation of intermediate II: 2-acetamido-4-chloro-6-acetonylphenol

[0046]Intermediate I (0.079kmol) and 32.0kg AlCl prepared by 18.0kg step one 3 (0.240kmol), 14.7kg NaCl (0.252kmol) were added to a 200...

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Abstract

The invention discloses a method for preparing 2-acetamido-6-acetylphenol. In the method, 2-amino-4-chlorophenol is taken as a main starting material, and the 2-acetamido-6-acetylphenol is prepared through acylation reaction, rearrangement reaction and hydrogenation reaction. The method comprises the following steps: a. acylation reaction: carrying out acylation reaction between the 2-amino-4-chlorophenol and acetyl chloride in a solvent to generate an intermediate I; b. rearrangement reaction: adding the intermediate I, AlCl3 and a cosolvent to a vessel, heating for reacting to generate an intermediate II, and extracting the purified intermediate II; and c. hydrogenation reaction: adding the intermediate II, Pd/C, an acid binding agent and a solvent to the reaction vessel, heating and introducing hydrogen, reacting to obtain the target product, and extracting and purifying the target product. The method has the advantages of wide and available raw material source, short synthetic route, low cost, less pollution and the like, and is applicable to large-scale production.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to a method for preparing 2-acetamido-6-acetonylphenol. Background technique [0002] Pranlukast (Pranlukast) is a leukotriene antagonist developed by Ono Pharmaceutical Co., Ltd. of Japan. It is used for the treatment of bronchial asthma. It was launched in Japan in 1995. Bronchial asthma is a common disease of the respiratory system and frequently-occurring disease. , Prankast has a therapeutic effect on bronchial asthma by blocking the combination of leukotriene receptors and leukotriene C4, D4, E4. Compared with similar products on the market, the curative effect of this product is better than that of ibudilast (Ibudilast) , Zafirlukast (Zafirlukast), which is characterized in that the lung function of the patient is significantly improved, and the dosage of corticosteroids and bronchodilators can be reduced. The structural formula of pranlukast is: [0003] [0004] 2-ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/33C07C231/12
Inventor 邹小伟安劲松裴玉琼戚长生
Owner 中国中化股份有限公司
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