Preparation method of 2-chloro-6-methoxy-3-methylpyridine

A kind of methylpyridine and methoxyl technology, applied in the field of organic chemical synthesis, can solve the problem that there is no literature report 2-chloro-6-methoxy-3-methylpyridine preparation method, chlorination temperature and chlorinating agent sensitivity , the problem of high production and operation cost, to achieve the effect of low cost, good stability and less by-products

Inactive Publication Date: 2017-07-07
CHEMSHUTTLE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Positional chlorination of pyridine is difficult, especially the direct substitution of the 2-position parent hydrogen. When carried out in the high-temperature gas phase, the reaction is sensitive to the chlorination temperature and the chlorination agent. The chlorination products are often mixtures, with different yields and comparative production and operation costs. high
[0005] There is no document reporting the preparation method of 2-chloro-6-methoxy-3-methylpyridine

Method used

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  • Preparation method of 2-chloro-6-methoxy-3-methylpyridine

Examples

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Embodiment 1

[0024] A preparation method of 2-chloro-6-methoxy-3-methylpyridine, said preparation method comprising the steps of:

[0025] (1) Add 2-methoxy-5-methylpyridine (50g, 0.4mol) and 40% hydrogen peroxide (100mL) into the solvent acetic acid (300mL) and mix them, and react for 1h at 80°C. The reaction solution was poured into crushed ice, and kept stirring, and then extracted with dichloromethane. After the organic phase was concentrated, 55 grams of a white solid product was obtained, that is, the 2-methoxy-5-methylpyridine-N-oxide (Yield 97%, content 96%).

[0026] (2) Add 2-methoxy-5-methylpyridine-N-oxide (50g, 0.36mol) and phosphorus oxychloride (200mL) into carbon tetrachloride (250mL) and mix them at 50°C 5h, after the reaction was completed, the solvent was removed by rotary evaporation, and then the reaction product was poured into crushed ice and kept stirring, then extracted with dichloromethane, and the organic phase was washed, dried, and concentrated to obtain 48g o...

Embodiment 2

[0029] A preparation method of 2-chloro-6-methoxy-3-methylpyridine, said preparation method comprising the steps of:

[0030] (1) Add 2-methoxy-5-picoline (50g, 0.4mol) and carbamide peroxide (330g, 3.5mol) into the solvent trifluoroacetic anhydride (250mL) and mix them, and react at 120°C for 15h, After the reaction was completed, the reaction solution was poured into crushed ice, and kept stirring, then extracted with dichloromethane, and after the organic phase was concentrated, 56 grams of a white solid product was obtained, that is, the 2-methoxy-5-picoline- N-oxide (yield 99%, content 97%).

[0031] (2) Add 2-methoxy-5-methylpyridine-N-oxide (50g, 0.36mol) and thionyl chloride (300mL) into dichloroethane (200mL) and mix, and react at 80°C 18h, after the reaction was completed, the solvent was removed by rotary evaporation, and then the reaction product was poured into crushed ice and stirred continuously, then extracted with dichloromethane, and the organic phase was wa...

Embodiment 3

[0033] A preparation method of 2-chloro-6-methoxy-3-methylpyridine, said preparation method comprising the steps of:

[0034] (1) Add 2-methoxy-5-methylpyridine (50g, 0.4mol) and m-chloroperoxybenzoic acid (1.3kg, 8.0mol) into the solvent trifluoroacetic acid (500mL) and mix them at 150°C After the reaction was completed, the reaction solution was poured into crushed ice and kept stirring, then extracted with dichloromethane, and after the organic phase was concentrated, 52 grams of a white solid product was obtained, namely the 2-methoxy-5-methanol Pyridine-N-oxide (yield 92%, content 97%).

[0035] (2) Add 2-methoxy-5-methylpyridine-N-oxide (50g, 0.36mol) and phosphorus oxychloride (750g, 3.6mol) into chloroform (250mL) and mix, and react at 130°C 5h, after the reaction was completed, the solvent was removed by rotary evaporation, and then the reaction product was poured into crushed ice and stirred continuously, then extracted with dichloromethane, and the organic phase wa...

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Abstract

The invention discloses a preparation method of 2-chloro-6-methoxy-3-methylpyridine. The preparation method comprises the following steps that (1), 2-methoxy-5-methylpyridine-N-oxide is prepared through a N-oxidization reaction of 2-methoxy-5-methylpyridine; (2), 2-chloro-6-methoxy-3-methylpyridine is obtained through a chlorination reaction of 2-methoxy-5-methylpyridine-N-oxide obtained in the step (1). The preparation method has the advantages of being short in process route, simple to operate, low in cost, easy to realize industrialization, high in yield, and easy in product purifying.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for preparing 2-chloro-6-methoxy-3-picoline from 2-methoxy-5-picoline through nitrogen oxidation and chlorination . Background technique [0002] The introduction of chlorine substituent groups into organic compounds has very important application value in the fields of biochemistry, pesticides, and functional materials due to the special properties of chloropyridine compounds. Two-substituted chlorpyridine is an important intermediate of fine chemical products, widely used in daily chemical industry and other fields, mainly used as an anti-dandruff agent in the field of daily chemical, it has the functions of antipruritic, anti-dandruff, reducing hair loss and protecting Hair color and other effects, currently the world's famous brands of shampoo all use it as an anti-dandruff and anti-itching ingredient. In addition, a variety of important drugs ca...

Claims

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Application Information

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IPC IPC(8): C07D213/64
CPCC07D213/64
Inventor 李欢鲍亮
Owner CHEMSHUTTLE
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