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Method for preparing brominated 1-benzyl-3-carboxypyridine and preparation method thereof

A technology of carboxypyridine and benzyl bromide, which is applied in the field of preparation of 1-benzyl-3-carboxypyridine bromide, can solve problems such as environmental pollution, achieve the effects of shortening reaction time, avoiding pollution and energy consumption, and simple purification

Inactive Publication Date: 2012-06-13
DONGYANG WEIDA ENVIRONMENTAL PROTECTION AUXILIARYCO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is to provide a preparation method of 1-benzyl-3-carboxypyridine bromide, which makes the reaction more complete and the product is easier to purify; environmental pollution problems

Method used

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  • Method for preparing brominated 1-benzyl-3-carboxypyridine and preparation method thereof

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Effect test

Embodiment 1

[0013] Niacin (123 grams, 1 mole), benzyl bromide (180 grams, 1.05 moles), and 2500 milliliters of acetonitrile were added in a 5000 milliliter reaction flask equipped with a stirring and reflux device, heated to reflux for reaction, and cooled to room temperature after the reaction. After filtering, the solid was washed twice with 200 ml of acetonitrile. The obtained mother liquor was recovered in a 5000 ml reaction flask, the obtained crude product was added into a beaker containing 1200 ml of distilled water, heated and dissolved, 10 grams of activated carbon was added, heated and boiled for 10 minutes, filtered while hot, the filtrate was cooled to crystallize, filtered, and vacuum-dried , 214.2 g of white crystals—1-benzyl-3-carboxypyridine bromide were obtained, with a yield of 72.8%.

Embodiment 2

[0015] Add nicotinic acid (123 grams, 1 mole), benzyl bromide (205 grams, 1.2 moles), and 2500 milliliters of acetonitrile into a 5000 milliliter reaction flask equipped with a stirring and reflux device, heat to reflux and cool to room temperature after the reaction is complete, filter , the solid was washed twice with 200 ml of acetonitrile. Gained mother liquor is reclaimed in the 5000 milliliter reaction bottle, and gained thick product joins in the beaker that 1200 milliliters of distilled waters are housed, heats to dissolve, adds 10 grams of gacs, heats and boils for 10 minutes, filters while it is hot, filtrate cooling crystallization, filtration, vacuum drying, 228.3 g of white crystals—1-benzyl-3-carboxypyridine bromide were obtained, with a yield of 77.6%.

Embodiment 3

[0017] Add nicotinic acid (123 grams, 1 mole), benzyl bromide (222 grams, 1.3 moles), and 2500 milliliters of acetonitrile into a 5000 milliliter reaction bottle equipped with a stirring and reflux device, heat to reflux for reaction, and cool to room temperature after the reaction is complete , filtered, and the solid was washed twice with 200 ml of acetonitrile. Gained mother liquor is reclaimed in the 5000 milliliter reaction bottle, and gained thick product joins in the beaker that 1200 milliliters of distilled waters are housed, heats and dissolves, adds 10 grams of gacs, heats and boils for 10 minutes, filters while hot, filtrate cooling crystallization, filtration, vacuum drying, 236.5 g of white crystals—1-benzyl-3-carboxypyridine bromide were obtained, with a yield of 80.4%.

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Abstract

The invention discloses a preparation method of brominated 1-benzyl-3-carboxypyridine, which obtains the brominated 1-benzyl-3-carboxypyridine by using acetonitrile as a reaction solvent and by reacting benzyl bromide in an excessive amount with niacin, separating a coarse solid product from solvent through room-temperature filtration after the reaction is accomplished, and purifying the coarse solid product by distilled water recrystallization. Because the technical scheme is adopted in the invention, the excessive amount of benzyl bromide adopted to react with niacin accelerates reaction speed, reduces reaction time, ensures that all niacin participates in reaction, avoids excessive niacin from being wrapped in the product, and makes the purification of the product simpler; meanwhile, a mother liquid cycling technique adopted by the invention allows the solvent to be directly utilized without distillation and purification and prevents pollution and energy consumption from a solvent recovery process are avoided; and thus, the preparation method has obvious environment-protection and economic benefits.

Description

technical field [0001] The invention relates to a preparation method of 1-benzyl-3-carboxypyridine bromide. Background technique [0002] 1-Benzyl-3-carboxypyridinium bromide is an excellent cyanide-free zinc plating brightener, and also an important pharmaceutical intermediate, which is produced by domestic and foreign enterprises. At present, there are two main production processes for this product: 1. Using N,N-dimethylformamide as a solvent, reacting an equivalent amount of nicotinic acid and benzyl bromide at 50°C, after the reaction is completed, distill under reduced pressure Recover N,N-dimethylformamide, and recrystallize the residue with water to obtain a white solid product (WO2005054198, US2007105810, WO2007132179); 2. Using acetonitrile as a solvent, use an equivalent amount of nicotinic acid and benzyl bromide under reflux conditions After the reaction, the solvent was recovered by distillation, and the solid was recrystallized with a mixed solvent of acetic a...

Claims

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Application Information

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IPC IPC(8): C07D213/803
Inventor 肖孝辉何颖峰王军华蒋跃平许技华
Owner DONGYANG WEIDA ENVIRONMENTAL PROTECTION AUXILIARYCO
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