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Preparation method of 3-amino-4-methylpyridine

A picoline and amino technology, applied in the field of organic chemical synthesis, can solve the problems of difficult preparation, harsh reaction conditions, and low product yield, and achieve the effects of simple reaction process, mild reaction conditions, and high product yield

Active Publication Date: 2015-02-18
JIANGSU ZHONGBANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Though these two kinds of methods all have higher yield, former method reaction condition is harsh, N 2 o 5 It is difficult to prepare; the reaction time of the first two steps of the latter route is long, and trifluoroacetic anhydride, which is expensive and cannot be recycled, is also used in the reaction; the above two methods are difficult to realize industrial production
[0006] In summary, in the existing methods for synthesizing 3-amino-4-picoline, many have the disadvantages of long reaction route, low product yield and harsh reaction conditions

Method used

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  • Preparation method of 3-amino-4-methylpyridine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a flask equipped with a mechanical stirring device, add 27.4g (0.2mol) of 4-picoline-3-boronic acid, 50ml of methanol, 128g (1mol) of ammonia (mass concentration 28%), 2.9g (0.02mol) of oxynitride Copper, start stirring, and the reaction is completed in 2 hours at room temperature (TLC monitors the reaction process). After suction filtration, the filtrate was concentrated under reduced pressure, and the obtained solid was recrystallized with ethyl acetate to obtain 20.5 g of 3-amino-4-methylpyridine, with a yield of 95%.

[0021] Example 1

[0022] In a flask equipped with a mechanical stirring device, add 27.4g (0.2mol) of 4-picoline-3-boronic acid, 50ml of methanol, 128g (1mol) of ammonia (mass concentration 28%), 2.3g (0.01mol) of silver oxide , Stirring was started, and the reaction was completed in 1 h at room temperature (TLC monitored the reaction process). After suction filtration, the filtrate was concentrated under reduced pressure, and the obtained solid...

Embodiment 3

[0024] In a flask equipped with a mechanical stirring device, add 27.4g (0.2mol) 4-picoline-3-boronic acid, 50ml acetonitrile, 75ml water, 39.6g (0.3mol) ammonium sulfate, 1.6g (0.02mol) copper oxide , Stirring was started, and the reaction was completed in 4 h at room temperature (TLC monitored the reaction process). After suction filtration, the filtrate was concentrated under reduced pressure, and the obtained solid was recrystallized with ethyl acetate to obtain 18.3 g of 3-amino-4-methylpyridine, with a yield of 85%.

Embodiment 4

[0026] In a flask equipped with a mechanical stirring device, add 27.4g (0.2mol) 4-picoline-3-boronic acid, 100ml ethanol, 100ml water, 21.4g (0.4mol) ammonium chloride, 1.6g (0.04mol) oxidation Zinc, start stirring, and the reaction is completed in 6 hours at room temperature (TLC monitors the reaction process). After suction filtration, the filtrate was concentrated under reduced pressure, and the obtained solid was recrystallized with ethyl acetate to obtain 18.1 g of 3-amino-4-methylpyridine, with a yield of 84%.

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Abstract

The invention belongs to the field of organic chemical synthesis and particularly relates to a synthesis method of 3-amino-4-methylpyridine which is an intermediate of an anti-AIDS drug nevirapine. According to the method, 4-methylpyridine-3-boronic acid is used as a raw material, an inorganic amide is used as an ammonia source and obtain3-amino-4-methylpyridine is prepared through one-step reaction in the presence of metal oxide as a catalyst. The preparation method is still simple and provides a new way for novel and efficient synthesis of 3-amino-4-methylpyridine and the disadvantages of long traditional route, low yield and severe reaction conditions are overcome.

Description

technical field [0001] The present invention relates to a synthesis method of an intermediate of anti-AIDS drug nevirapine—3-amino-4-methylpyridine, in particular to a method for synthesizing 3-amino-4-methylpyridine with 4-methylpyridine-3-boronic acid and ammonia The method for base pyridine belongs to the field of organic chemical synthesis. Background technique [0002] 2-Chloro-3-amino-4-picoline is a key intermediate in the synthesis of anti-AIDS drug nevirapine. 2-Chloro-3-amino-4-picoline can be obtained by chlorination of 3-amino-4-picoline, US5200522, US5668287, US5686618 and J.Heterocycl.Chem.;38(1):99-104;2001 reported that starting from 3-amino-4-picoline, using Cl 2 or HCl and H 2 o 2 Chlorination can give 2-chloro-3-amino-4-picoline in high yield. Therefore, the key step in the synthesis of 2-chloro-3-amino-4-picoline lies in the synthesis of 3-amino-4-picoline. At present, the synthetic method of relevant 3-amino-4-picoline at home and abroad can roughl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 薛谊陈洪龙赵华阳岳瑞宽徐强李维思肖云
Owner JIANGSU ZHONGBANG PHARMA
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