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Preparation method of 2-chloro-5-methylpyridine

A kind of methylpyridine and amino technology, applied in the field of preparation of 2-chloro-5-methylpyridine, can solve problems such as low yield, and achieve the effect of improving yield

Inactive Publication Date: 2017-01-04
NANJING REDSUN BIOCHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the low yield problem in the existing 2-amino-5-picoline synthesis technology of 2-chloro-5-picoline, to provide a preparation of 2-chloro-5-picoline method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] At room temperature, in a 250mL four-neck flask, add 150g of dichloromethane as a solvent, 10.8g (0.1mol) of 2-amino-5-picoline, stir and dissolve, then add 9.2g (0.06mol) of phosphorus oxychloride dropwise, It takes 20 minutes. After the dropwise addition was completed, 7.9 g (0.12 mol) of nitrosyl chloride was introduced at a reaction temperature of 30-35° C. for 30 minutes, and then kept for 20 minutes. The reaction product was neutralized with liquid caustic soda at room temperature, and the obtained organic phase was extracted with dichloromethane and rectified to obtain 12.0 g (0.094 mol) of 2-chloro-5-picoline, with a yield of 94% and a purity of 99%.

Embodiment 2

[0023] At room temperature, add 100 g of solvent dichloromethane and 10.8 g (0.1 mol) of 2-amino-5-methylpyridine into a 250 mL four-necked flask, and stir to dissolve. 7.65 g (0.05 mol) of phosphorus oxychloride was added dropwise, and 7.9 g (0.12 mol) of nitrosyl chloride was introduced at the same time. The reaction temperature was 30-35° C. for 30 minutes, and then kept for 20 minutes. The reaction product was neutralized with liquid caustic soda at room temperature, and the obtained organic phase was extracted by methylene chloride and rectified to obtain 11.9 g (0.093 mol) of 2-chloro-5-picoline, with a yield of 93% and a purity of 99%.

Embodiment 3

[0025] The solvent was replaced by dichloromethane with p-chlorotrifluorotoluene, the reaction temperature was increased to 70-80°C, and other conditions were the same as in Example 1 to obtain 12.0 g (0.094 mol) of 2-chloro-5-methylpyridine, with a yield of 94%. , 99% purity.

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Abstract

The invention discloses a preparation method of 2-chloro-5-methylpyridine, and belongs to the field of organic chemistry. According to the method, 2-amino-5-methylpyridine serves as the raw material and reacts with nitrosyl chloride under the existence of acyl chloride, and 2-chloro-5-methylpyridine is obtained. The production process is simple and convenient, the yield is high, and when metered based on 2-amino-5-methylpyridine, the yield can reach 94%.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a preparation method of 2-chloro-5-picoline. Background technique [0002] 2-Chloro-5-picoline is an important pharmaceutical and pesticide intermediate. It can be used to produce medicines such as the anti-AIDS drug Tipranavir. It can also be used to produce insecticides with high efficiency, broad spectrum, safety and novel mechanism of action, such as imidacloprid and acetamiprid. [0003] The existing synthetic methods of 2-chloro-5-picoline mainly include 3-picoline direct chlorination method, 3-picoline oxidative chlorination method, 2-amino-5-picoline chlorination method, and cyclochlorination. [0004] The Sandmeyer Reaction is a common and important method for the preparation of chlorinated aromatics. In the method, an aromatic diazonium salt is generated by reacting aromatic amine, nitrite and excess hydrochloric acid, and then chlorinated aromatic hydro...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 薛谊丁永山钟劲松王文奎蒋剑华
Owner NANJING REDSUN BIOCHEM CO LTD
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