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Preparation method of isopropyl 2-(3-nitrophenylmethylene)acetacetate

A technology of isopropyl acetoacetate and nitrobenzylidene is applied in the field of preparation of pharmaceutical intermediate compounds, can solve the problems of low yield and high reaction temperature, achieve high yield, mild reaction conditions, and reduce production cost effect

Inactive Publication Date: 2012-07-11
SICHUAN KELUN PHARMA RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are following deficiencies in this method: (1) yield is low, (2) reaction temperature is relatively high

Method used

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  • Preparation method of isopropyl 2-(3-nitrophenylmethylene)acetacetate
  • Preparation method of isopropyl 2-(3-nitrophenylmethylene)acetacetate
  • Preparation method of isopropyl 2-(3-nitrophenylmethylene)acetacetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add m-nitrobenzaldehyde (151g, 1.0mol) and isopropyl acetoacetate (144g, 1.0mol) in a three-necked flask equipped with mechanical stirring, reflux condenser, and thermometer, and dissolve in 500ml isopropanol, add 14.5g Catalytic amount of piperidinium acetate, stirred at -20~-10°C for 24h, and left overnight. After filtration, 21.61g of the finished product was obtained, with a yield of 78%.

Embodiment 2

[0042] Add m-nitrobenzaldehyde (151g, 1.0mol) and isopropyl acetoacetate (144g, 1.0mol) in a three-necked flask equipped with mechanical stirring, reflux condenser, and thermometer, and dissolve in 500ml isopropanol, add 14.5g Catalytic amount of piperidinium acetate, stirred at -10~5°C for 4 hours, and left overnight. After filtration, 23.27g of the finished product was obtained, with a yield of 84%.

Embodiment 3

[0044] Add m-nitrobenzaldehyde (151g, 1.0mol) and isopropyl acetoacetate (144g, 1.0mol) in a three-necked flask equipped with mechanical stirring, reflux condenser, and thermometer, and dissolve in 500ml isopropanol, add 14.5g Catalytic amount of piperidinium acetate, stirred at 5-45°C for 1h, and left overnight. After filtration, 22.16g of the finished product was obtained, with a yield of 80%.

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PUM

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Abstract

The invention relates to a preparation method of isopropyl 2-(3-nitrophenylmethylene)acetacetate, particularly a preparation method of an azelnidipine intermediate isopropyl 2-(3-nitrophenylmethylene)acetacetate, which comprises the following steps: taking 130-170 parts by weight of nitrobenzaldehyde and 130-160 parts by weight of isopropyl acetacetate, dissolving in 500-1000 parts by volume of solvent, adding 1.45-145 parts by weight of catalytic amount of piperidine acetate, stirring at -20-45 DEG C for 1-24 hours, standing, and filtering to obtain the isopropyl 2-(3-nitrophenylmethylene)acetacetate. The solvent is one of C1-C4 alcohol, acetone, butanone, tetrahydrofuran, dioxane, benzene, methylbenzene, xylene, dichloromethane, chloroform, n-hexane, cyclohexane, acetonitrile and DMF (N,N-dimethylformamide).

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate compound, in particular to a preparation method of an azedipine intermediate, namely 2-(3-nitrobenzylidene) isopropyl acetoacetate. Background technique [0002] Azeldipine, the chemical name is 3,5-pyridinedicarboxylic acid, 1,4-dihydropyridine-2-amino-6-methyl-4-(3-nitrophenyl)-, 3-(1- (Benzhydryl)-3-azetidinyl) 5-(1-methylethyl) ester, (±). Its chemical structural formula is as follows: [0003] [0004] Azedipine is a new generation of calcium antagonist developed by Japan SANKYO Co., Ltd. This product was approved for marketing in Japan in 2003, and it is mainly used clinically for the treatment of hypertension. [0005] 2-(3-nitrobenzylidene) isopropyl acetoacetate is an important intermediate for the preparation of Azelnidipine, and its structural formula is as follows: [0006] [0007] The synthetic route of existing 2-(3-nitrobenzylidene) isopropyl acetoac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/56C07C201/12
Inventor 黄耀宗潘野杨琪林奉儒梁隆程志鹏
Owner SICHUAN KELUN PHARMA RES INST CO LTD
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