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A method for preparing isradipine key intermediate 4-formylbenzofura

A technology of formylbenzene and isradipine is applied in the field of preparing isradipine key intermediate 4-formylbenzofuran, which can solve the problem of affecting the quality and yield of target product, destruction of benzfuraze, and generation of by-products. and other problems, to achieve the effect of improving yield, reducing the production of by-products, and improving quality

Inactive Publication Date: 2011-12-14
SHANDONG INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the long reaction time, it is easy to cause damage to benzofurase, produce by-products, and affect the quality and yield of the target product.

Method used

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  • A method for preparing isradipine key intermediate 4-formylbenzofura
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  • A method for preparing isradipine key intermediate 4-formylbenzofura

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Experimental program
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Effect test

specific Embodiment approach 2

[0026] In 600ml ethanol, add 80.3g (0.275mol) 4-(dibromomethyl) benzofura, the silver nitrate solution that 187g silver nitrate and 90ml water are made into. The mixed solution was heated to 70°C, reacted for 1 hour, and filtered to remove the formed inorganic salts. 1042ml of p-toluenesulfonic acid was added to the above filtrate, and after stirring for 30 minutes, the organic solvent ethanol was distilled off. The remaining aqueous solution was diluted with 1000ml of water, and the resulting product was extracted with 400ml×2 dichloromethane. The dichloromethane solution was washed with 100ml×2 water, 80ml of 15% sodium bicarbonate solution, and 100ml of water, respectively, and dried with anhydrous sodium sulfate. The organic solvent dichloromethane was distilled off, and the remaining solid was recrystallized with cyclohexane to obtain 29.8 g of the target product with a yield of 73.1%.

specific Embodiment approach 3

[0027] In 800ml isopropanol, add 80.3g (0.275mol) 4-(dibromomethyl) benzofura, the silver nitrate solution that 187g silver nitrate and 90ml water are made into. The mixed solution was heated to 70°C, reacted for 1 hour, and filtered to remove the formed inorganic salts. 980ml of 20% hydrochloric acid solution was added to the filtrate, and after stirring for 30 minutes, the organic solvent isopropanol was distilled off. The remaining aqueous solution was diluted with 1000ml of water. The resulting product was extracted with 400ml x 2 dichloromethane. The dichloromethane solution was washed with 100ml×2 water, 80ml of 15% sodium bicarbonate solution, and 100ml of water, respectively, and dried with anhydrous sodium sulfate. The organic solvent dichloromethane was distilled off, and the remaining solid was recrystallized with cyclohexane to obtain 26.6 g of the product with a yield of 65.4%.

specific Embodiment approach 4

[0028] In 400ml methanol, add 80.3g (0.275mol) 4-(dibromomethyl) benzofura, the silver nitrate solution that 187g silver nitrate and 90ml water are made into. The mixed solution was heated to 70°C, reacted for 1 hour, and filtered to remove the formed inorganic salts. 980ml of 20% hydrochloric acid solution was added to the filtrate, and after stirring for 30 minutes, the organic solvent methanol was distilled off. The remaining aqueous solution was diluted with 1000ml of water. The resulting product was extracted with 400ml x 2 dichloromethane. The dichloromethane solution was washed with 100ml×2 water, 80ml 15% sodium bicarbonate solution, and 100ml water respectively, and dried with anhydrous sodium sulfate. The organic solvent dichloromethane was distilled off, and the remaining solid was recrystallized with cyclohexane to obtain 30.6 g of the product with a yield of 75.2%.

[0029] Description of drawings:

[0030] figure 1 It is a flow chart of the preparation met...

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Abstract

The invention discloses a novel preparation method of an isradipine key intermediate 4-formoxylbenzofuran. According to the invention, 4-(bisbromomethyl) benzofuran reacts in a mixed system of silver nitrate aqueous solution and organic alcoholic solution to generate a nitric acid ester intermediate; the intermediate product, without being separated, can directly and mildly hydrolyze under an acidic condition to obtain the 4-formoxylbenzofuran.

Description

technical field [0001] The invention relates to a method for preparing isradipine key intermediate 4-formylbenzofura. Isradipine is clinically used in the treatment of hypertensive disorders. Background technique [0002] Isradipine, also known as isradipine, iradipine, its English name is isradipine, and its chemical name is 4-(4-benzofuryl)-1,4-dihydro-2,6-dimethyl- Methyl-1-methylethyl 3,5-pyridinedicarboxylate. Its structural formula is as follows: [0003] [0004] Isradipine is a new type of dihydropyridine calcium channel blocker, which was developed by the Swiss company Sandoz. It was first listed in the UK in 1989, and recently the United States and Japan have also successively approved production. Isradipine belongs to a new generation of antihypertensive products. It has obvious antihypertensive effect and anti-atherosclerosis effect. Dipine takes effect slowly (2 to 4 weeks) and lasts for a long time. By maintaining or restoring the subcutaneous blood flow...

Claims

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Application Information

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IPC IPC(8): C07D271/12
Inventor 张兰英林振广张广洲曹冲
Owner SHANDONG INST OF PHARMA IND
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