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Preparation method of 2-chlorin-3-amido-4-methyl pyridine

A kind of methylpyridine and amino technology, which is applied in the synthesis field of 2-chloro-3-amino-4-methylpyridine, can solve the problems such as unobtainable raw materials, high equipment requirements, cumbersome steps and the like

Inactive Publication Date: 2008-04-09
范锦荣
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are not easy to get, and the steps are cumbersome. It needs to be chlorinated at the 2,6-position of the intermediate 2,6-dihydroxy-4-methyl-3-cyanopyridine, and then dechlorinated. Rechlorination at the 2-position with chlorine gas
2, 6-position chlorination and dechlorination reduction and selective 2-position chlorination steps, equipment requirements are relatively high, the cost is expensive, and the yield is unstable
This method yield is low, and the one-step productive rate of ring closure is very low, is 30.4% (Grozinger Karl. CA2318412(2000), EP1070053(2000)

Method used

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  • Preparation method of 2-chlorin-3-amido-4-methyl pyridine
  • Preparation method of 2-chlorin-3-amido-4-methyl pyridine
  • Preparation method of 2-chlorin-3-amido-4-methyl pyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Preparation of sodium but-3-en-2-one-4-alcohol

[0028]

[0029] Put 40mL of methanol into a 500mL four-neck flask, cool it down, then add 0.2mol 27% sodium methoxide, and stir to make it completely dissolve. Then, a mixed solution of 0.34 mol of methyl formate and 13.0 g (0.2 mol) of acetone was added dropwise at 25°C. Afterwards, it was kept in a water bath at 40° C. for 3 hours to obtain 20.0 g of sodium but-3-en-2-one-4-olate with a purity of 98.8% and a yield of 92.6%.

[0030] (2) Preparation of 4,4-dimethoxybutan-2-one

[0031]

[0032] In the four-necked flask connected with a thermometer, an air inlet pipe and an exhaust pipe, first add 50mL of methanol, and then add concentrated sulfuric acid dropwise to make the pH of the solution 0-3. Then, 21.6 g of sodium but-3-en-2-one-4-oxide was added dropwise under ice cooling. After dripping, it was transferred to a water bath at 85°C and refluxed for 3h. Afterwards, neutralize with 20% NaOH solution und...

Embodiment 2

[0048] (1) Preparation of sodium but-3-en-2-one-4-alcohol

[0049] Synthesized according to the method and conditions of Example 1 (1), only methyl formate was replaced by ethyl formate to obtain but-3-en-2-one-4-alcohol sodium with a purity of 99.3% and a yield of 92.5%.

[0050] (2) Preparation of 4,4-dimethoxybutan-2-one

[0051] Synthesize as in Example 1 (2) method and conditions.

[0052] (3) Condensate 4,4-dicyano-3-methyl-3-butene dimethyl acetal and 1,1-dicyano-4-methoxy-2-methyl-1,3- Preparation of butadiene

[0053] Synthesize as in Example 1 (3) method and conditions.

[0054] (4) Preparation of 3-cyano-4-methylpyridin-2-one

[0055] Synthesize as in Example 1 (4) method and conditions.

[0056] (5) Preparation of 2-chloro-3-cyano-4-methylpyridine

[0057] Synthesize as in Example 1 (5) method and conditions.

[0058] (6) Preparation of 2-chloro-4-methylpyridine-3-carboxamide

[0059] Synthesize as in Example 1 (6) method and conditions.

[0060] (7) Prepa...

Embodiment 3

[0063] (1) Preparation of sodium but-3-en-2-one-4-alcohol

[0064] Synthesized according to the method and conditions of Example 1 (1), only methyl formate was replaced by propyl formate to obtain but-3-en-2-one-4-alcohol sodium with a purity of 98.3% and a yield of 91.2%.

[0065] (2) Preparation of 4,4-dimethoxybutan-2-one

[0066] Synthesize as in Example 1 (2) method and conditions.

[0067] (3) Condensate 4,4-dicyano-3-methyl-3-butene dimethyl acetal and 1,1-dicyano-4-methoxy-2-methyl-1,3- Preparation of butadiene

[0068] Synthesize as in Example 1 (3) method and conditions, only malononitrile is replaced by cyanoacetamide to obtain a condensate.

[0069] (4) Preparation of 3-cyano-4-methylpyridin-2-one

[0070] Synthesize as in Example 1 (4) method and conditions.

[0071] (5) Preparation of 2-chloro-3-cyano-4-methylpyridine

[0072] Synthesize as in Example 1 (5) method and conditions.

[0073] (6) Preparation of 2-chloro-4-methylpyridine-3-carboxamide

[0074]...

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Abstract

The invention relates to a method for preparing 2-chlorin-3-amideo-4-picolyl. The invention has the practical proposal to solve the technical problems that acetone, sodium methoxide, formic ether are adopted as the raw materials during synthesizing the 2-chlorin-3-amideo-4-picolyl. After the seven steps including sodium salt, condensation, addition, cyclization, chlorination, hydrolysis and Hofmann degradation, the total output rate of the reaction is larger than 18.4 percent, and the product purity is above 99.7 percent.

Description

technical field [0001] The present invention relates to the synthesis method of 2-chloro-3-amino-4-picoline. Background technique [0002] In the domestic literature, there is no report about the preparation method of 2-chloro-3-amino-4-picoline so far. [0003] In 1980, Chapman et al. reported that 2-chloro-3-nitro-4-picoline was used as raw material to obtain 2-chloro-3-amino-4-picoline through reduction (Chapman et al.J. Chem. Soc. Perkin Trans. I, 1980: 2398-2404.). In 1993, Rozinger K.G. and others reported that 2-chloro-3 was obtained by ring closure, chlorination, hydrolysis, Hoffman degradation, hydrogenation and chlorination by using ethyl β-carbonyl butyrate and cyanoacetamide as starting materials. -Amino-4-picoline, crude yield 43.2-52.7%. The raw materials of this method are not easy to get, and the steps are cumbersome. It needs to be chlorinated at the 2,6-position of the intermediate 2,6-dihydroxy-4-methyl-3-cyanopyridine, and then dechlorinated. Rechlori...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
Inventor 范锦荣
Owner 范锦荣
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