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Method for preparing N-(5-chloro-8-quinolyl)benzamide compound by adopting electrochemical micro-channel reaction device

A technology of microchannel reaction and benzamide, which is applied in electrolysis process, electrolysis components, electrolysis organic production and other directions, can solve the problems of complicated steps and long reaction time, and achieves the effects of simple operation, shortened reaction time and improved yield.

Active Publication Date: 2020-08-11
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Purpose of the invention: the technical problem to be solved by this invention is to provide a method for preparing N-(5-chloro-8-quinolyl) benzamides using an electrochemical microchannel reaction device for the deficiencies in the prior art, The method can solve the problems of complicated steps and long reaction time in the reaction process, and can improve the reaction efficiency, and is suitable for industrial production

Method used

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  • Method for preparing N-(5-chloro-8-quinolyl)benzamide compound by adopting electrochemical micro-channel reaction device
  • Method for preparing N-(5-chloro-8-quinolyl)benzamide compound by adopting electrochemical micro-channel reaction device
  • Method for preparing N-(5-chloro-8-quinolyl)benzamide compound by adopting electrochemical micro-channel reaction device

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Effect test

Embodiment 1

[0045] Mix 24mmol (1.99g) of dichloromethane and 0.3mmol (0.06g) of copper acetate with 10mL of acetonitrile and water in a mixed solution (acetonitrile: water = 4:1, that is, 8mL of acetonitrile and 2mL of water) to obtain a homogeneous Solution I was added to syringe pump 1; 2.0 mmol (0.50 g) of N-(quinolin-8-yl) benzamide was dissolved in 10 mL of acetonitrile and water mixed solution (acetonitrile: water = 4: 1, ie 8mL of acetonitrile and 2mL of water) to obtain a homogeneous solution II, which was added to the syringe pump 2; the syringe pump 1 and the syringe pump 2 were used to inject solution I and solution II at a flow rate of 0.10mL / min and 0.15mL / min, respectively. Inject in the micro-mixer 3, enter the electrochemical microchannel reactor 4 after mixing in the micro-mixer 3 to react; the first microchannel reactor reaction volume is 1.25mL, and the reaction residence time is 5.0min; The temperature of the channel reactor is 25° C., and the reaction current is 100 m...

Embodiment 2

[0047] Mix 24mmol (1.99g) of dichloromethane and 0.3mmol (0.06g) of copper acetate with 10mL of acetonitrile and water in a mixed solution (acetonitrile: water = 4:1, that is, 8mL of acetonitrile and 2mL of water) to obtain a homogeneous Solution I was added to syringe pump 1; 2.0 mmol (0.50 g) of N-(quinolin-8-yl) benzamide was dissolved in 10 mL of acetonitrile and water mixed solution (acetonitrile: water = 4: 1, ie 8mL of acetonitrile and 2mL of water) to obtain a homogeneous solution II, which was added to the syringe pump 2; the syringe pump 1 and the syringe pump 2 were injected into the solutions I and II at a flow rate of 0.10mL / min and 0.15mL / min respectively. In the micromixer 3, after mixing in the micromixer 3, enter the electrochemical microchannel reactor 4 to react; the first microchannel reactor reaction volume is 1.25mL, and the reaction residence time is 5.0min; The temperature of the reactor is 25° C., and the reaction current is 80 mA; after the reaction i...

Embodiment 3

[0049] Mix 24mmol (1.99g) of dichloromethane and 0.3mmol (0.06g) of copper acetate with 10mL of acetonitrile and water in a mixed solution (acetonitrile: water = 4:1, that is, 8mL of acetonitrile and 2mL of water) to obtain a homogeneous Solution I was added to syringe pump 1; 2.0 mmol (0.50 g) of N-(quinolin-8-yl) benzamide was dissolved in 10 mL of a mixed solution of nitrile and water (acetonitrile: water = 4: 1, ie 8mL of acetonitrile and 2mL of water) to obtain a homogeneous solution II, which was added to the syringe pump 2; the syringe pump 1 and the syringe pump 2 were injected into the solutions I and II at a flow rate of 0.10mL / min and 0.15mL / min respectively. In the micromixer 3, after mixing in the micromixer 3, enter the electrochemical microchannel reactor 4 to react; the first microchannel reactor reaction volume is 1.25mL, and the reaction residence time is 5.0min; The temperature of the reactor is 25° C., and the reaction current is 120 mA; after the reaction ...

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Abstract

The invention discloses a method for preparing an N-(5-chloro-8-quinolyl)benzamide compound by adopting an electrochemical micro-channel reaction device, which comprises the following steps: dissolving an 8-(benzoylamino)quinoline compound in a first organic solvent to prepare a reaction solution A; dissolving dichloromethane and copper acetate in a second organic solvent, and preparing a reactionsolution B; respectively pumping the reaction solution A and the reaction solution B into a micro mixer of an electrochemical micro-channel reaction device at the same time for mixing, and then enabling the mixture to flow into a micro-reactor for reaction, thereby obtaining the product. Compared with the prior art, the method has the advantages that a traditional oxidizing agent is not needed, and a new method for electrocatalytically and selectively preparing the chloroquinoline compound by taking dichloromethane as a chlorination reagent through a micro-flow field is creatively developed;meanwhile, a micro-channel reaction device is utilized, so that the reaction time is greatly shortened, the reaction conversion rate is increased, and the yield is remarkably increased and reaches 85%.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for preparing N-(5-chloro-8-quinolyl)benzamide compounds by using an electrochemical microchannel reaction device. Background technique [0002] Halogenated aromatics and heterocyclic compounds are versatile building blocks for cross-couplings and Grignard reactions, enabling the construction of a wide variety of C-C, C-N, C-O and C-S compounds. In addition, aryl halides are frequently found in drug molecules, as biological properties are often significantly enhanced by the incorporation of halogen atoms. Traditionally, halogenated products are generated by electrophilic substitution of electron-rich arenes or heterocycles. The electronic properties of aromatic rings lead to inherent selectivity. Also, bihalogenated by-products are often unavoidable. Recently, regioselective halogenation has attracted increasing attention. And, ortho-metallatio...

Claims

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Application Information

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IPC IPC(8): C25B3/06C25B9/06C25B15/08C25B9/17
CPCC25B15/08C25B3/27C25B9/17
Inventor 郭凯刘成扣林鑫鑫方正曾翠莲叶凡胡超
Owner NANJING UNIV OF TECH
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