Efficient preparation of 4-dimethylaminopyridine

A technology of dimethylaminopyridine and cyanopyridine, which is applied in the field of one-pot preparation of DMAP, can solve problems affecting product yield, unstable intermediates, and increased side reactions, so as to avoid excessive time and reduce product loss , reduce the effect of side effects

Inactive Publication Date: 2014-05-14
ANHUI COSTAR BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The operation is relatively cumbersome, and the obtained intermediate is unstable, and it will decompose under the action of extern

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 200 Kg of 4-cyanopyridine, 107 Kg of acrylic acid, and 170 Kg of water in sequence into a 3000 L enamel glass reaction kettle, stir evenly, then add 260 Kg of concentrated hydrochloric acid dropwise, and keep at 50°C for 5 h. After cooling to room temperature, 150 Kg of dimethylformamide was added at one time and kept at 35°C for 2 h. Add 30% K dropwise after the heat preservation 2 CO 3 Solution, until the pH value is 10.5~13, keep it under reflux for 1 h. After the system was cooled, remove the water layer by suction filtration, wash the solid phase with water, and dry to obtain the finished product of 4-dimethylaminopyridine. The content of HPLC analysis was 99.24%, and the yield was 92.3%. mp110~111.6℃ (WRS-1A digital melting point apparatus).

Embodiment 2

[0024] Add 200 Kg of 4-cyanopyridine, 107 Kg of acrylic acid, and 170 Kg of water in sequence into a 3000 L enamel glass reaction kettle, stir evenly, then add 260 Kg of concentrated hydrochloric acid dropwise, and keep at 55°C for 4 h. After cooling to room temperature, 420 Kg of dimethylamine (33%) was added at one time and kept at 40°C for 1.5 h. After the incubation, 30% NaOH solution was added dropwise until the pH value was 11.5-12, and then incubated under reflux for 1.5 h. After cooling the system, remove the water layer by suction filtration, wash the solid phase with water, and dry to obtain the finished product of 4-dimethylaminopyridine. The HPLC analysis content is 98.6%, and the yield is 90.4%. mp111~111.9℃ (WRS-1A digital melting point apparatus).

Embodiment 3

[0026] Add 200 Kg of 4-cyanopyridine, 107 Kg of acrylic acid, and 170 Kg of water in sequence into a 3000 L enamel glass reaction kettle, stir evenly, then add 260 Kg of concentrated hydrochloric acid dropwise, and keep at 55°C for 6 h. After cooling to room temperature, 155 Kg of dimethyl hydrochloride was added at one time and kept at 35°C for 2 h. Add 30% Na dropwise after the heat preservation 2 CO 3 solution until the pH value was 11-12, and then incubated under reflux for 2 h. After the system was cooled, remove the water layer by suction filtration, wash the solid phase with water, and dry to obtain the finished product of 4-dimethylaminopyridine. The HPLC analysis content was 96.2%, and the yield was 87.3%. mp110.3~112.1℃ (WRS-1A digital melting point apparatus).

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Abstract

The invention discloses a new method for preparing 4-dimethylaminopyridine (DMAP) with a one-kettle process by taking 4-cyanopyridine and acrylic acid as main raw materials. The method mainly comprises the following steps: performing quaternization of 4-cyanopyridine with acrylic acid to obtain an intermediate; reacting with an amination reagent; neutralizing acid in the system in the presence of a pH regulator to enable the product to be free, wherein the reaction period is greatly shortened; and performing simple separation and purification to obtain a target product DMAP. In the method disclosed by the invention, the reaction conditions are mild, the synthesis method is simple, the DMAP synthesis can be efficiently performed through simple technological operation, and the obtained product has high purity and high yield; and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a new method for preparing DMAP by using 4-cyanopyridine and acrylic acid as main raw materials through a one-pot method. Background technique [0002] 4-Dimethylaminopyridine is a new type of high-efficiency acylation catalyst. reactions have been widely used. In addition, DMAP can also be used as an inverse phase transfer catalyst for interfacial reactions. Due to its fast reaction speed, mild conditions, wide range of applicable solvents, and high product yields, it is suitable for the acylation reaction of alcohols with large steric hindrance and some hydroxyl compounds that are unstable to acids. It is widely used in fine chemical production fields such as medicine, pesticide, spices, petrochemical industry, etc., and has broad application prospects. [0003] There are many ways to synthesize 4-dimethylaminopyridine. Usually the laboratory can be prepared by 4-substituted pyridine: such as 4-aminopyridine method, 4-tri...

Claims

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Application Information

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IPC IPC(8): C07D213/74
CPCC07D213/74
Inventor 刘善和方红新强金凤
Owner ANHUI COSTAR BIOCHEM CO LTD
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