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Preparation method of pranlukast intermediate

An intermediate, the technology of hydroxyacetophenone, applied in the field of preparation of pranlukast intermediate, can solve problems such as environmental pollution, achieve the effect of increasing reaction yield, reducing reaction activity, and streamlining process steps

Inactive Publication Date: 2020-11-20
太仓康源化建医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the serious problem of environmental pollution caused by the two-step method, the application provides a preparation method of pranlukast intermediate

Method used

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  • Preparation method of pranlukast intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A preparation method of pranlukast intermediate, comprising the following steps:

[0042] S1. Weigh 100g of 4-phenylbutoxybenzoic acid and put it into a three-necked flask with a capacity of 1L, add 3-amino-2-hydroxyacetophenone, 4-phenylbutoxybenzoic acid and 3-amino-2 -The mass ratio of hydroxyacetophenone is 1:0.56, then add 200g Polyethylene Glycol-400 to dissolve;

[0043] S2. Then add the phosphotungstic acid catalyst, the mass ratio of the added phosphotungstic acid catalyst to 4-phenylbutoxybenzoic acid is 0.008:1, stir and mix well, heat to 150°C under the condition of nitrogen protection, keep warm for 10h ;

[0044] S3. After the reaction is completed, cool to 8°C, add 400mL ether for extraction, let stand for stratification, keep the lower polyethylene glycol layer, spin-evaporate the separated upper ether layer, and recover the phosphotungstic acid catalyst;

[0045] S4, adding dilute nitric acid with a concentration of 0.05wt% to the polyethylene glycol ...

Embodiment 2-10

[0048] Embodiments 2-10 all relate to a preparation method of a pranlukast intermediate, based on Example 1, the difference is: the mass ratio of 4-phenylbutoxybenzoic acid and phosphotungstic acid catalyst in step S1, The mass ratio of 4-phenylbutoxybenzoic acid and 3-amino-2-hydroxyacetophenone is different from that of polyethylene glycol and 4-phenylbutoxybenzoic acid, and the specific values ​​are shown in the following table:

[0049] Table 1. The mass ratio of 4-phenylbutoxybenzoic acid to phosphotungstic acid catalyst, the mass ratio of 4-phenylbutoxybenzoic acid to 3-amino-2-hydroxyacetophenone and polyethylene glycol to 4- The concrete numerical value of the mass ratio of phenylbutoxybenzoic acid:

[0050]

Embodiment 11-18

[0052]Examples 11-18 all relate to a preparation method of a pranlukast intermediate, based on Example 10, the difference is that the reaction temperature and reaction time in step S2 are different, and the specific values ​​are shown in the following table:

[0053] Reaction temperature and reaction time in table 2. step S2:

[0054]

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Abstract

The invention relates to the field of medicine synthesis, and particularly discloses a preparation method of a pranlukast intermediate. The preparation method of the pranlukast intermediate comprisesthe following steps: taking 4-phenylbutoxy benzoic acid and 3-amino-2-hydroxyacetophenone as raw materials, adding a phosphotungstic acid catalyst into a reaction system, and carrying out amidation reaction to obtain a target product 3-[4-(4-phenylbutoxy)benzoylamino]-2-hydroxyacetophenone. The preparation method provided by the invention has the advantage of environmental protection on the premise of ensuring the yield and purity of the target product.

Description

technical field [0001] The application relates to the field of drug synthesis, more specifically, it relates to a preparation method of a pranlukast intermediate. Background technique [0002] Pranlukast is a drug for treating bronchial asthma. It selectively binds and antagonizes leukotriene receptors to inhibit bronchoconstriction, vascular hyperpermeability, mucosal edema and airway allergic reaction. [0003] At present, the important intermediate of pranlukast, 3-[4-(4-phenylbutoxy)benzoylamino]-2-hydroxyacetophenone, is usually prepared in two steps, with 4-phenylbutoxy Benzoic acid and 3-amino-2-hydroxyacetophenone are raw materials, carry out amidation reaction, and concrete reaction steps are as follows: [0004] 4-phenylbutoxybenzoic acid is generally first activated with active agents such as thionyl chloride to form a mixed acid, and then amidated with the amino group on 3-amino-2-hydroxyacetophenone to obtain the target product 3-[4 -(4-Phenylbutoxy)benzoylami...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/22
CPCC07C221/00C07C225/22
Inventor 马兴元王屹皓王霖龙姜琪
Owner 太仓康源化建医药有限公司
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