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Industrial preparation method of pantoprazole intermediate pyridine hydrochloride

A technology of pyridine hydrochloride and pantoprazole, applied in the field of medicine, can solve the problems of high cost, unfavorable industrial production, low yield and the like, and achieve the effects of easy handling, low price and cost reduction

Inactive Publication Date: 2010-11-03
南京元德新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] We know that 2-chloromethyl-3,4-lutidine hydrochloride is an important intermediate for the preparation of pantoprazole, and its preparation method is generally: use 2-methyl-3-hydroxypyridine as The raw materials are synthesized through seven steps of methylation, nitration, methoxylation, etc., but the raw materials used in this method are not domestic products. If furan is used as raw material to synthesize by itself, the yield is low and the cost is high, which is not conducive to industrial production.

Method used

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  • Industrial preparation method of pantoprazole intermediate pyridine hydrochloride
  • Industrial preparation method of pantoprazole intermediate pyridine hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0027] (1) Preparation of 3-methoxy-2-methyl-4H-pyran-4-one

[0028] Dissolve 140g of sodium hydroxide in 250g of water, then add 141g of maltol, stir until dissolved, raise the temperature to 84°C, slowly add 19g of dimethyl sulfate dropwise, control the dropping temperature at 84-85°C, and use 30 % sodium hydroxide solution to adjust the pH value to about 11. After the dropwise addition, the temperature was raised to 96 ° C, kept for 13 hours, and the temperature was lowered to below 30 ° C to obtain 130 g of orange-yellow liquid 3-methoxy-2-methyl-4H-pyridine Furan-4-one;

[0029] (2) Preparation of 3-methoxy-2-methyl-4(1H)-pyridone

[0030] Add 140g of 3-methoxy-2-methyl-4H-pyran-4 ketone to 1700g of ammonia water, stir at 85°C for 16 hours, then distill off the water under reduced pressure and dry to obtain 130g of brown solid 3-methoxy- 2-Methyl-4(1H)-pyridone, yield 93%;

[0031] (3) Preparation of 4-chloro-3-methoxy-2-picoline

[0032] Put 139g of 3-methoxyl-2-meth...

example 2

[0042] (1) Preparation of 3-methoxy-2-methyl-4H-pyran-4-one

[0043] Dissolve 230g of sodium hydroxide in 410g of water, then add 231g of maltol, stir until dissolved, raise the temperature to 84°C, slowly add 312g of dimethyl sulfate dropwise, control the dropping temperature at 80°C, and use 30% hydrogen Adjust the pH value of the sodium oxide solution to keep it at about 11, raise the temperature to 92°C after the dropwise addition, keep the temperature for 13 hours, and cool down to below 30°C to obtain 210g of orange-yellow liquid 3-methoxy-2-methyl-4H-pyran -4 ketone;

[0044] (2) Preparation of 3-methoxy-2-methyl-4(1H)-pyridone

[0045] Add 210g of 3-methoxy-2-methyl-4H-pyran-4one to 2550g of ammonia water, stir at 80°C for 16 hours, then distill off the water under reduced pressure and dry to obtain 198g of brown-yellow solid 3-methoxy -2-Methyl-4(1H)-pyridone, yield 93.9%;

[0046] (3) Preparation of 4-chloro-3-methoxy-2-picoline

[0047] Put 180g of 3-methoxy-2-m...

example 3

[0057] (1) Preparation of 3-methoxy-2-methyl-4H-pyran-4-one

[0058] Dissolve 160g of sodium hydroxide in 285g of water, add 159g of maltol, stir until dissolved, raise the temperature to 86°C, slowly add 218g of dimethyl sulfate dropwise, control the dropping temperature at 85°C, and use 30% hydrogen Adjust the pH value of the sodium oxide solution to keep it at about 11. After the dropwise addition, the temperature was raised to 96°C, kept for 13 hours, and the temperature was lowered to below 30°C to obtain 148g of orange-yellow liquid 3-methoxy-2-methyl-4H-pyran -4 ketone;

[0059] (2) Preparation of 3-methoxy-2-methyl-4(1H)-pyridone

[0060] Add 175g of 3-methoxy-2-methyl-4H-pyran-4one to 2100g of ammonia water, stir at 85°C for 16 hours, then distill off the water under reduced pressure and dry to obtain 164g of brown-yellow solid 3-methoxy -2-Methyl-4(1H)-pyridone, yield 93.5%;

[0061] (3) Preparation of 4-chloro-3-methoxy-2-picoline

[0062] Put 125g of 3-methoxyl...

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Abstract

The invention discloses an industrial preparation method of pantoprazole intermediate pyridine hydrochloride, including the following steps: (1) preparation of 3-methoxy-2-methyl-4H-pyran-4-ketone; (2) preparation of 3-methoxy-2-methyl-4(1H)-pyridone; (3) preparation of 4-chlorine-3-methoxy-2-methylpyridine; (4) preparation of 4-chlorine-3-methoxy-2-methylpyridine-N-oxide; (5) preparation of 3, 4-dimethoxy-2-methylpridine-N-oxide; (6) preparation of 2-hydroxymethyl-3, 4-dimethoxyprindine; (7) preparation of 2-chloromethyl-3, 4-dimethxyl pyridine hydrochloride. In the invention, the reactions in the steps are all carried out under atmospheric pressure while temperature is lower than 100 DEG C, condition is mild, thus being safe and reliable; besides, the raw materials adopted in the invention are all low in price and high in utilization ratio, and multiple raw materials can be used repeatedly, thus reducing cost; and the quality of the obtained product can reach more than 98%, thus completely meeting the requirement; in addition, waste gas and waste water which are produced in the steps are easy to be treated, thus being applicable to industrialized production.

Description

Technical field [0001] The invention relates to an industrial production method of pyridine hydrochloride, an important intermediate of pantoprazole, and belongs to the field of medical technology. Background technique [0002] Proton pump inhibitors are used to treat gastrointestinal ulcers related to gastric acid. They are a major development in medicine in recent years. Since the advent of the first proton pump inhibitor, omeprazole, proton pump inhibitors have been used to treat gastroduodenal ulcers. The method has been established by a large number of clinical trials at home and abroad, and pantoprazole is the third proton pump inhibitor approved for marketing developed by the German company Byk Culden. Because it is more effective than omeprazole and omeprazole under weakly acidic conditions, Lansoprazole is more stable and has less impact on other combined drugs, so it has broad market prospects. [0003] We know that 2-chloromethyl-3,4-dimethylpyridine hydrochlorid...

Claims

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Application Information

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IPC IPC(8): C07D213/69
Inventor 李华
Owner 南京元德新材料科技有限公司
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