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Method for preparing N-substituted pyrrolidone derivative

A technology for pyrrolidone and derivatives, which is applied in the field of preparing N-substituted pyrrolidone derivatives, can solve problems such as complex synthesis methods, and achieve the effects of simple operation, high yield, and mild reaction conditions

Active Publication Date: 2021-09-17
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis method in the related art is relatively complicated

Method used

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  • Method for preparing N-substituted pyrrolidone derivative
  • Method for preparing N-substituted pyrrolidone derivative
  • Method for preparing N-substituted pyrrolidone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis of 2-phenylisoindol-1-one:

[0049]

[0050] Take a three-neck round bottom flask, add 75mg (0.50mmol) of o-formylbenzoic acid, 70mg (0.75mmol) of aniline, 169.5mg (0.5mmol) of tetra-n-butyl ammonium hydrogensulfate, and 5mL of N,N-dimethylformamide, The carbon rod was used as the anode, and the carbon rod was used as the cathode, and the electrochemical reaction was carried out at room temperature (about 25° C.) and 10 mA current for 5 hours. After the reaction, add 20 mL of ethyl acetate and 100 mL of water for extraction, collect the organic phase after layering, and extract the water phase twice with ethyl acetate, each time the amount of ethyl acetate is 10 mL, combine the organic phases, add anhydrous sodium sulfate to dry , The solvent was distilled off under reduced pressure, and the product was obtained by column chromatography with a yield of 81%.

[0051] The characterization data for the product are:

[0052] 1 H NMR (500MHz, CDCl ...

Embodiment 2

[0055] Example 2: Synthesis of 2-(p-tolyl)isoindol-1-one:

[0056]

[0057] Take a three-neck round bottom flask, add 75mg (0.50mmol) of o-formylbenzoic acid, 107mg (1mmol) of p-methylaniline, 169.5mg (0.5mmol) of tetra-n-butyl ammonium hydrogensulfate, and N,N-dimethylformamide 5mL, with a carbon rod as the anode and a carbon rod as the cathode, electrochemically react at room temperature and 8mA for 5 hours. After the reaction, add 20 mL of ethyl acetate and 100 mL of water for extraction, collect the organic phase after layering, and extract the water phase twice with ethyl acetate, each time the amount of ethyl acetate is 10 mL, combine the organic phases, add anhydrous sodium sulfate to dry , The solvent was distilled off under reduced pressure, and the product was obtained by column chromatography with a yield of 83%.

[0058] The characterization data for the product are:

[0059] 1 H NMR (500MHz, Chloroform-d (CDCl 3 ))δ=7.95-7.91(m,1H),7.74(d,J=5.8Hz,2H),7.58(d...

Embodiment 3

[0062] Example 3: Synthesis of 2-(4-butylphenyl)isoindol-1-one:

[0063]

[0064] Take a three-neck round bottom flask, add 75mg (0.50mmol) of o-formylbenzoic acid, 112mg (0.75mmol) of p-n-butylaniline, 169.5mg (0.5mmol) of tetra-n-butyl ammonium hydrogensulfate, N,N-dimethyl Formamide 5mL, carbon rod as anode, carbon rod as cathode, electrochemical reaction at room temperature and 7mA current for 5 hours. After the reaction, add 20 mL of ethyl acetate and 100 mL of water for extraction, collect the organic phase after layering, and extract the water phase twice with ethyl acetate, each time the amount of ethyl acetate is 10 mL, combine the organic phases, add anhydrous sodium sulfate to dry , The solvent was distilled off under reduced pressure, and the product was obtained by column chromatography with a yield of 60%.

[0065] The characterization data for the product are:

[0066] 1 H NMR (500MHz, Chloroform-d) δ = 7.94 (dd, J = 7.2, 1.4Hz, 1H), 7.79-7.76 (m, 2H), 7.6...

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Abstract

The invention discloses a method for preparing an N-substituted pyrrolidone derivative, which comprises the following steps: adding an amine compound and a benzoic acid compound into an electrolysis system for reaction to prepare the N-substituted pyrrolidone derivative. The invention provides an external oxidant-free electro-catalysis preparation method, which is characterized in that an amine compound and a benzoic acid compound are utilized to synthesize an N-substituted pyrrolidone derivative in one step through an electro-catalysis reaction. The method is relatively high in yield, does not need to use a metal catalyst and an external oxidant, is green and environment-friendly, and is low in price; the electrolysis system and reaction raw materials used in the reaction are low in price, post-treatment is simple and convenient, and the method is suitable for industrial production; besides, the method is mild in reaction condition, simple to operate and high in yield.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing N-substituted pyrrolidone derivatives. Background technique [0002] Pyrrolidone derivatives are important structural units in organic chemistry and have applications in various dissolved oxygen main components, such as surfactants, intermediates of inks, fibers and pharmaceuticals. N-substituted pyrrolidone derivatives have attracted much attention due to their wide application in the fields of solvents, surfactants, drug racemic statins, and their utilization in biomass valorization. However, the synthesis method in the related art is relatively complicated. [0003] Therefore, it is necessary to develop a method for preparing N-substituted pyrrolidone derivatives, which is highly efficient and environmentally friendly. Contents of the invention [0004] The technical problem to be solved by the present invention is to provide an electrocata...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/05C25B3/09
CPCC25B3/05C25B3/09
Inventor 黄玉冰邹子荣李亚枚邬宏婷
Owner WUYI UNIV
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