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Synthesis method of 5-bromo-2-methyl 4-hydroxypyridinecarboxylate

A technology of hydroxyisonicotinic acid and methyl ester, applied in the field of chemistry, can solve the problems of low total yield, no literature report on the synthesis method, difficulty in large-scale industrial production, etc., and achieves simple and easy operation of reaction steps and safe and reliable reaction process. , cheap effect

Inactive Publication Date: 2012-01-18
QILU UNIV OF TECH
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Problems solved by technology

[0002] 5-bromo-2-hydroxyisonicotinate (Methyl 5-bromo-2-hydroxyisonicotinate) is an important pharmaceutical intermediate, but its synthetic method has not been reported in the literature
[0003] The above-mentioned preparation method of 2-amino-5-bromoisonicotinate has the disadvantages of low yield and difficult purification of the product, making it difficult to realize large-scale industrial production
According to the relevant yield of the prior art, if 2-amino-5-bromoisonicotinic acid methyl ester is carried out diazotization hydrolysis synthesis 5-bromo-2-hydroxyisonicotinic acid methyl ester, it can be expected that 5-bromo-2- The overall yield of hydroxyisonicotinic acid will be lower

Method used

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  • Synthesis method of 5-bromo-2-methyl 4-hydroxypyridinecarboxylate
  • Synthesis method of 5-bromo-2-methyl 4-hydroxypyridinecarboxylate

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Embodiment 1

[0037] (1) Synthesis of 5-bromo-4-methyl-2-nitropyridine

[0038]Slowly add 1500ml of concentrated sulfuric acid (98.3% in mass fraction) dropwise into a 5L Erlenmeyer flask containing 750ml of 30% hydrogen peroxide. During the addition, the temperature is controlled to be less than or equal to 20°C. After the addition, cool to Standby at 5°C; add 0.535mol 2-amino-5-bromo-4-picoline to 2550ml of concentrated sulfuric acid, and cool down to zero; slowly add the stock solution prepared in the previous step to the mixture, and control the temperature at 5°C ℃15℃, stirring at 5℃15℃ after dripping for 30 minutes, then reacting at room temperature for 3 hours; after the reaction, pour the reaction solution into the ice-water mixture, adjust the pH to 7-8 with NaOH solution, and precipitate a large amount of light yellow The solid was filtered with suction, and the filter cake was washed with a small amount of water; dried at 45°C to obtain 104.6 g of 5-bromo-4-methyl-2-nitropyridine...

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Abstract

The invention provides a synthesis method of 5-bromo-2-methyl 4-hydroxypyridinecarboxylate. 5-bromo-2-methyl 4-hydroxypyridinecarboxylate is prepared by five-step reaction namely two-step oxygen, esterification, reduction, diazotization hydrolysis and the like by taking 2-amino-5-bromo-4-methylpyridine as a raw material, wherein the total yield is more than 40%. According to the invention, the raw material is available, a used intermediate is cheap in price, reaction steps are simple and easy to operate, reaction process is safe and reliable, and the yield of the product is high, thus the synthesis method has potential industrial application value.

Description

technical field [0001] The invention relates to a method for synthesizing methyl 5-bromo-2-hydroxyisonicotinate, belonging to the technical field of chemistry. Background technique [0002] 5-bromo-2-hydroxyisonicotinate (Methyl 5-bromo-2-hydroxyisonicotinate) is an important pharmaceutical intermediate, but its synthesis method has not been reported in the literature. We provide a method for preparing 5-bromo-2-hydroxyisonicotinic acid methyl ester by diazotization hydrolysis of 2-amino-5-bromoisonicotinic acid methyl ester. The prior art method for synthesizing 2-amino-5-bromoisonicotinic acid methyl is to take 2-amino-isonicotinic acid methyl ester as raw material to synthesize 2-amino-5-bromoisonicotinic acid methyl through bromination, such as : WO2007 / 11326 international published patent application discloses the method for synthesizing 2-amino-5-bromoisonicotinic acid methyl ester with N-bromosuccinimide (N-bromosuccinimide, NBS) as bromination agent, product The cr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/803
Inventor 张大同霍领雁
Owner QILU UNIV OF TECH
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