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Synthesis method of 5-chloro-3-cyano-4-methony-2-(1H)-pyridinone

A synthetic method, methoxyl technology, applied in the direction of organic chemistry, can solve the problems of low product purity, difficulty in purification, incomplete reaction of raw materials, etc., and achieve the effect of high product purity and easy purification

Inactive Publication Date: 2014-03-26
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing synthesis process of 5-chloro-3-cyano-4-methoxy-2(1H)pyridone has the defects of incomplete reaction of raw materials, low product purity and difficult purification

Method used

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  • Synthesis method of 5-chloro-3-cyano-4-methony-2-(1H)-pyridinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Ingredients:

[0017] ①3-cyano-4-methoxy-2(1 H)pyridone 20g

[0018] ②thionyl chloride 100ml

[0019] Operation: Slowly drop thionyl chloride into 3-cyano-4-methoxy-2(1 H)pyridone at a temperature of 0-5°C, keep the temperature below 5°C, drop thionyl chloride Accelerate at 1.5 ml / min, then slowly raise the temperature until reflux occurs, keep the reaction for 6 hours, evaporate the thionyl chloride to dryness under reduced pressure, add 100ml of n-hexane to beat the solid for 1 hour, filter, and dry to obtain the product. The yield is 92.7%.

[0020] The density of the obtained product: 1.434g / cm3, the boiling point under the pressure of 760 mmHg is: 376.845°C, and the flash point is 181.709°C.

Embodiment 2

[0022] Ingredients:

[0023] ①3-cyano-4-methoxy-2(1 H)pyridone 20g

[0024] ②thionyl chloride 100ml

[0025] Operation: Slowly drop thionyl chloride into 3-cyano-4-methoxy-2(1 H)pyridone at a temperature of 0-5°C, keep the temperature below 5°C, drop thionyl chloride The acceleration is 1.2ml / min, and then the temperature is raised slowly until reflux occurs, and the reaction is kept for 6.5 hours. The thionyl chloride is evaporated to dryness under reduced pressure, and 100ml of n-hexane is added to beat the solid for 1 hour, filtered, and dried to obtain the product. The yield is 91.4%.

[0026] Density of the resulting product: 1.432g / cm 3， , The boiling point at 760 mmHg pressure is: 376.795°C, and the flash point is 181.694°C.

Embodiment 3

[0028] Ingredients:

[0029] ①3-cyano-4-methoxy-2(1 H)pyridone 20g

[0030] ②thionyl chloride 100ml

[0031] Operation: Slowly drop thionyl chloride into 3-cyano-4-methoxy-2(1 H)pyridone at a temperature of 0-5°C, keep the temperature below 5°C, drop thionyl chloride Accelerate at 2.0ml / min, then slowly raise the temperature until reflux occurs, keep the reaction for 5.5 hours, evaporate the thionyl chloride to dryness under reduced pressure, add 100ml of n-hexane to beat the solid for 1 hour, filter, and dry to obtain the product. The yield is 92.7%.

[0032] Density of the resulting product: 1.438g / cm 3， , The boiling point at 760 mmHg pressure is: 376.892°C, and the flash point is 181.796°C.

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of 5-chloro-3-cyano-4-methony-2-(1H)-pyridinone. The synthesis method comprises the following steps: thionyl chloride is slowly dropped in 3-cyano-4-methony-2-(1H)-pyridinone at the temperature ranging from 0 DEG C to 5 DEG C, the additive amount of thionyl chloride is 5 ml per gram of the 3-cyano-4-methony-2-(1H)-pyridinone, the dropping speed is 1.2-2.0 ml / min, then the temperature is slowly increased until backflow is generated, the heat preservation reaction is performed for 5.5-6.5 hours, thionyl chloride is subjected to pressure reduction and evaporation drying, normal hexane is added, the solids are subjected to pulping for 1 hour, the additive amount of normal hexane is 5 ml per gram of 3-cyano-4-methony-2-(1H)-pyridinone, and filtering and drying are performed, so that 5-chloro-3-cyano-4-methony-2-(1H)-pyridinone is obtained. The synthesis method has the advantages of thorough raw material reaction, high product purity and easiness in purification.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of 5-chloro-3-cyano-4-methoxy-2(1H)pyridone. Background technique [0002] 5-Chloro-3-cyano-4-methoxy-2(1 H)pyridone is an important intermediate in the synthesis of drug gimester. It is one of the components of the anticancer drug S-1, which can inhibit the toxic and side effects of the anticancer drug tegafur. S-1 is an oral anticancer agent of fluorouracil derivatives, which consists of three components: tegafur (Tegafur, FT), Gimeracil and oxonate potassium (PotassiumOXOnate, oteracil OXO). Ratio 1:0.4:1 ratio composition. The mechanism of action of these three components: FT is a prodrug of 5-Fu, which has excellent oral bioavailability and can be converted into 5-Fu in vivo. By inhibiting thymidylate synthase, it prevents the conversion of deoxyuridine to deoxythymidylate, thereby interfering with DNA synthesis. CDHP can inhibit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/85
Inventor 尤晓明李洋张国栋王显涛延云峰魏文祥
Owner QILU UNIV OF TECH
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