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A method for preparing n-(5-chloro-8-quinolyl) benzamides using an electrochemical microchannel reaction device

A microchannel reaction and electrochemical technology, which is applied in the direction of electrolytic components, electrolytic process, electrolytic organic production, etc., can solve the problems of complicated steps and long reaction time, and achieve the effect of simple operation, shortened reaction time and easy separation

Active Publication Date: 2021-06-29
NANJING TECH UNIV
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  • Summary
  • 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

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  • A method for preparing n-(5-chloro-8-quinolyl) benzamides using an electrochemical microchannel reaction device
  • A method for preparing n-(5-chloro-8-quinolyl) benzamides using an electrochemical microchannel reaction device
  • A method for preparing n-(5-chloro-8-quinolyl) benzamides using an electrochemical microchannel reaction device

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Experimental program
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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 N-(5-chloro-8-quinolyl) benzamide compounds by using an electrochemical microchannel reaction device. The 8-(benzoylamino) quinoline compounds are dissolved in The first organic solvent is made into reaction solution A; dichloromethane and copper acetate are dissolved in the second organic solvent to make reaction solution B; reaction solution A and reaction solution B are pumped into the electrochemical microchannel reaction device simultaneously respectively Mix in a micro-mixer, then flow into a micro-reactor for reaction, and obtain the product. Compared with the prior art, the present invention does not need traditional oxidants, and creatively develops a new method for the electrocatalytic selective preparation of chloroquinolines using dichloromethane as a chlorination reagent microflow field; at the same time, the present invention utilizes The microchannel reaction device greatly shortens the reaction time, improves the reaction conversion rate, and significantly increases the yield to 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] Haloarenes and heterocycles are versatile building blocks for cross-couplings and Grignard reactions, allowing for 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-metallation-halogen quenchi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/27C25B3/05C25B3/07C25B3/09C25B3/11C25B9/17C25B15/08
CPCC25B15/08C25B3/27C25B9/17
Inventor 郭凯刘成扣林鑫鑫方正曾翠莲叶凡胡超
Owner NANJING TECH UNIV
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