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Novel process for preparing 3-(substituted benzoyl) butyric acid

A benzoyl and new process technology, applied in the field of preparation of pimobendan intermediate 3-butyric acid, can solve the problems of difficult waste disposal, long route, high cost, etc., and achieve easy separation and purification, high yield and low cost Effect

Inactive Publication Date: 2010-05-12
北京信益泰医药科技开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It overcomes the shortcomings of the existing synthetic methods such as long route, difficult waste disposal, low yield and high cost

Method used

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  • Novel process for preparing 3-(substituted benzoyl) butyric acid
  • Novel process for preparing 3-(substituted benzoyl) butyric acid
  • Novel process for preparing 3-(substituted benzoyl) butyric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] 50ml round bottom flask, add 5ml of dioxane, 1.00g (5.9mmol) of p-chloropropiophenone, 0.82g (8.9mmol) of oxoacetic acid, and stir until all the solids are dissolved. Add dropwise 0.70g (7.1mmol) of 98% concentrated sulfuric acid ). Heated to reflux. After 20h, the reaction was complete. Cooled to room temperature, evaporated the solvent under reduced pressure, poured the mixture into water, a solid precipitated out, filtered to obtain 1.22g of the yellow solid product 3-p-chlorobenzoyl-2-butenoic acid , yield 71%, melting point 130~132℃.

Embodiment 2

[0032]

[0033] 100ml there-necked flask, add 5.00g (22.26mmol) of 3-p-chlorobenzoyl-2-butenoic acid, 27ml of glacial acetic acid, 1ml of water, stir and add 2.90g (44.62mmol) of Zn powder. Heat to reflux. The reaction was complete after 1 h. Cool to room temperature, filter, pour the reaction solution into 250ml of water, extract with dichloromethane (100ml×3), combine the organic phases, evaporate the solvent under reduced pressure, and dry to obtain a light yellow solid product 3-p-chlorobenzoylbutanoic acid 4.20 g, yield 83%, melting point 84-85°C.

Embodiment 3

[0035]

[0036] Add 17ml of fuming nitric acid to a 50ml three-neck flask, cool down to -15°C, add 7.00g (30.88mmol) of 3-p-chlorobenzoylbutyric acid in batches, and stir at -15 to -10°C for reaction. After 4h the reaction was complete. The reaction solution was poured into 200ml of crushed ice, stirred thoroughly, and filtered to obtain 6.30g of white solid product 3-(3-nitro-4-chlorobenzoyl)butanoic acid with a yield of 75.1% and a melting point of 118-121°C.

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Abstract

The invention provides a novel process, which takes substituted propiophenone and oxoacetic acid as starting raw materials, carries out condensation to obtain 3-(substituted benzoyl)-2-butenoic acid, and carries out reduction and nitrification to obtain a pimobendan intermediate 3-(substituted benzoyl) butyric acid. The method has the advantages of few steps, easy and simple operation, easy separation and purification of products, high yield and low cost, uses common reagents, and is the novel process suitable for industrialized production.

Description

technical field [0001] The invention relates to a new process for preparing pimobendan intermediate 3-(substituted benzoyl)butyric acid. Background technique [0002] 3-(Substituted benzoyl)butyric acid is an intermediate of the cardiac stimulant pimobendan. [0003] Pimobendan (Pimobendan, Fig. 1) is a cardiotonic drug with vasodilation effect developed by Boechringer Ingelhem of Germany. It is a phosphodiesterase inhibitor and was first launched in Japan in 1994. It is mainly used clinically for cardiac The clinical efficacy of moderate and mild congestive heart failure is better than that of captopril. [0004] [0005] Fig.1Pimobendan [0006] In 1960, W.H.Puterbaugh et al. described in J.Amer.Chem.Soc.Vol.82, 3635, 1960 a method for the synthesis of 3-(3-nitro-4-chlorobenzoyl)butanoic acid using a two-step reaction. Although the method has a short route, expensive lithium amide is used as a reagent, which is not suitable for industrial production due to high cost....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/88C07C51/373C07C51/347C07C205/56C07C201/12
CPCY02P20/55
Inventor 冯文化张克勤姜英俊聂靖东王栋伟
Owner 北京信益泰医药科技开发有限公司
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