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Synthesis method of 2, 6-dimethyl-4-bromopyridine

A technology of lutidine and a synthesis method, which is applied in the synthesis field of 2,6-dimethyl-4-bromopyridine, can solve the problems of low yield and long process route, and achieves high yield and short process route. , the effect of easy availability of raw materials

Inactive Publication Date: 2019-05-14
丹阳市中润检测技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthetic method of reported 2,6-dimethyl-4-bromopyridine has disadvantages such as low yield and long process route.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0012] Diethyl malonate reacts with sodium to form a salt, then add dropwise the toluene solution of 4-nitro-2-methyl-6 chloropyridine for condensation reaction, and then decarboxylate under acidic conditions to obtain 4-nitro-2,6 - Lutidine; wherein the molar ratio of diethyl malonate, alkali metal, 4-nitro-2-methyl-6-chloropyridine is 5:1.1:1.

[0013] 4-nitro-2,6-lutidine was catalyzed by Pd / C, methanol was used as a solvent, hydrogenation reduction, suction filtration, and the filtrate was concentrated to obtain 4-amino-2,6-lutidine;

[0014] 4-Amino-2,6-lutidine first forms a salt with an acid, cools to -15°C, adds liquid bromine dropwise, and then adds sodium nitrite aqueous solution dropwise, after the dropwise addition, adjust the pH of the solution to be alkaline, and then carry out Extraction, drying and concentration give 2,6-dimethyl-4-bromopyridine.

Embodiment approach 2

[0016] Diethyl malonate reacts with potassium to form a salt, then add dropwise the toluene solution of 4-nitro-2-methyl-6 chloropyridine for condensation reaction, and then decarboxylate under acidic conditions to obtain 4-nitro-2,6 - Lutidine; wherein the molar ratio of diethyl malonate, alkali metal, 4-nitro-2-methyl-6-chloropyridine is 6:1.3:1.

[0017] 4-nitro-2,6-lutidine was catalyzed by Pd / C, methanol was used as a solvent, hydrogenation reduction, suction filtration, and the filtrate was concentrated to obtain 4-amino-2,6-lutidine;

[0018] 4-Amino-2,6-lutidine first forms a salt with an acid, cools to -6°C, adds liquid bromine dropwise, and then adds sodium nitrite aqueous solution dropwise, after the dropwise addition, adjust the pH of the solution to be alkaline, and then carry out Extraction, drying and concentration give 2,6-dimethyl-4-bromopyridine.

Embodiment approach 3

[0020] Diethyl malonate reacts with sodium to form a salt, then add dropwise the toluene solution of 4-nitro-2-methyl-6 chloropyridine for condensation reaction, and then decarboxylate under acidic conditions to obtain 4-nitro-2,6 - lutidine; wherein the molar ratio of diethyl malonate, alkali metal, 4-nitro-2-methyl-6-chloropyridine is 5.4:1.2:1.

[0021] 4-nitro-2,6-lutidine was catalyzed by Pd / C, methanol was used as a solvent, hydrogenation reduction, suction filtration, and the filtrate was concentrated to obtain 4-amino-2,6-lutidine;

[0022] 4-Amino-2,6-lutidine first forms a salt with acid, cools to 3°C, adds liquid bromine dropwise, and then adds sodium nitrite aqueous solution dropwise, adjusts the pH of the solution to be alkaline after the dropwise addition, and then proceeds to extraction , dried and concentrated to obtain 2,6-dimethyl-4-bromopyridine.

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Abstract

The invention relates to the field of organic chemistry, in particular to a synthesis method of 2, 6-dimethyl-4-bromopyridine. The method includes following steps: allowing diethyl malnoate and alkalimetal to be in reaction to generate salt, dropwise adding a methylbenzene solution of 4 nitro-2-methyl-6 chloropyridine for condensation reaction, and decarboxylating in an acidic condition to obtain4-nitro-2, 6-dimethylpyridine; allowing 4-nitro-2, 6-dimethylpyridine to be catalyzed by Pd / C, taking methanol as a solvent, performing hydrogenation reduction and suction filtering, and concentrating filtrate to obtain 4-amino-2, 6-dimethylpyridine; enabling 4-amino-2, 6-dimethylpyridine and acid to generate salt, cooling to -15-3 DEG C, dropwise adding liquid bromine, dropwise adding a sodium nitrite water solution after dropwise adding is completed, adjusting pH of the solution to be alkaline after dropwise adding is completed, extracting, drying, and concentrating to obtain 2, 6-dimethyl-4-bromopyridine. The method has the advantages of being mild in reaction condition, high in yield, easy-to-get in raw material, low in cost and short in process route and having industrialization prospect.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a synthesis method of 2,6-dimethyl-4-bromopyridine. Background technique [0002] Pyridine and its derivatives are widely distributed in nature. Many plant components such as alkaloids contain pyridine ring compounds in their structures, which are the basis for the production of many important compounds, such as medicines, pesticides, dyes, surfactants, rubber additives, feed additives, food additives, adhesives, etc. Indispensable raw material in production. 2,6-Dimethyl-4-bromopyridine is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, organic solvents, and can also be used in dye production, pesticide production and spices. At present, the reported synthetic methods of 2,6-dimethyl-4-bromopyridine have disadvantages such as low yield and long process route. Contents of the invention [0003] The technical pro...

Claims

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Application Information

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IPC IPC(8): C07D213/61
Inventor 魏倩
Owner 丹阳市中润检测技术有限公司
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