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Method for preparing 2-pyrrolidone through guided catalytic oxidation

A pyrrolidone and catalytic oxidation technology, applied in organic chemistry and other fields, can solve the problems of inability to realize gram-level reactions, expensive catalysts, low yield, etc., and achieve the effects of being suitable for large-scale industrial production, solving chemical selectivity, and solving expensive prices

Pending Publication Date: 2022-07-29
YANGTZE NORMAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1. The gram-level reaction cannot be realized; 2. The catalyst is very expensive and difficult to use industrially; 3. The yield of the reaction is low, that is, the catalytic efficiency is low

Method used

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  • Method for preparing 2-pyrrolidone through guided catalytic oxidation
  • Method for preparing 2-pyrrolidone through guided catalytic oxidation
  • Method for preparing 2-pyrrolidone through guided catalytic oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] see Image 6 , put compound 1 (0.2 mmol, 48.3 mg), Pd(OAc)2 (10 mol%, 4.5 mg), Oxone (123 mg), 1.0 mL DCE (dichloroethane solvent) in a 15 mL Schnike tube, And carry out argon pumping. Next, after the vigorously stirred reaction mixture was reacted at 130 degrees for 24 hours, compound 2 was obtained. Next, the mixture containing compound 2 was hydrolyzed by 2 equivalents of an aqueous solution of potassium hydroxide to obtain the target product 3 (12.5 mg, total 75% yield).

Embodiment 2

[0049] see Figure 7 , put compound 1 (0.2 mmol, 48.3 mg), Pd(OAc)2 (10 mol%, 4.5 mg), Oxone (123 mg), 1.0 mL MeCN (acetonitrile organic solvent) in a 15 mL Schnike tube, and carry out Argon gas extraction and ventilation. Next, compound 2 was obtained after the vigorously stirred reaction mixture was reacted at 130 degrees for 48 hours. Next, the mixture containing compound 2 was hydrolyzed by 2 equivalents of potassium hydroxide in water to obtain the target product 3 (12.0 mg, total 70% yield).

Embodiment 3

[0051] see Figure 8 , put compound 1 (0.2 mmol, 48.3 mg), Pd(MeCN)2Cl2 (10 mol%, 5.2 mg), Oxone (123 mg), 1.0 mL DCE in a 15 mL Schnike tube, and carry out argon purge gas. Next, compound 2 was obtained after the vigorously stirred reaction mixture was reacted at 130 degrees for 48 hours. Next, the mixture containing compound 2 was hydrolyzed by 2 equivalents of an aqueous solution of potassium hydroxide to obtain the target product 3 (10.0 mg, total 59% yield).

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Abstract

The invention relates to the technical field of 2-pyrrolidone preparation, in particular to a method for preparing 2-pyrrolidone through guided catalytic oxidation. The method comprises the following steps: placing a compound 1, a Pd catalyst and an oxidizing agent in a solvent, and generating a compound 2 under an argon protection condition; and hydrolyzing the compound 2 with an aqueous solution of potassium hydroxide to obtain the target product 2-pyrrolidone. Catalytic reaction is carried out through the palladium catalyst, the problem that an existing catalyst is high in price can be effectively solved, and the method is more suitable for large-scale industrial production. By means of the guiding group, the chemical selectivity of the reaction is solved, and meanwhile the catalytic efficiency of the reaction is improved.

Description

technical field [0001] The invention relates to the technical field of preparation of 2-pyrrolidone, in particular to a method for preparing 2-pyrrolidone by guided catalytic oxidation. Background technique [0002] Refer to the drawings in the description figure 1 , 2-pyrrolidone skeleton, as a basic structural unit, widely exists in natural products and drugs, and has important application value. It is often used as a basic chemical raw material and drug fragment in medicine, textile, dyes, coatings, It is widely used in cosmetics and other industries, such as the manufacture of Naofukang, nylon 4, polyvinylpyrrolidone, artificial plasma, etc. In addition, 2-pyrrolidone can be used as a basic synthon for organic synthesis (such as the construction of 1-vinyl-2-pyrrolidone, etc.). In particular, it can be directly used as a small molecule drug, potentially for anticancer (Phytother Res. 2013, 27, 1664.). In addition, 2-pyrrolidone derivatives have different biological ac...

Claims

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Application Information

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IPC IPC(8): C07D207/267
CPCC07D207/267Y02P20/584
Inventor 苟铨谢剑锋冉星陶兰邱学文冉子怡杨克林李晓彤
Owner YANGTZE NORMAL UNIVERSITY