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A kind of method for n-hydroxyphthalimide catalyzed electrolytic synthesis of fluorenone

A hydroxyphthalimide, catalytic electrolysis technology, applied in electrolysis components, electrolysis process, electrolysis organic production and other directions, to achieve the effect of low emission of "three wastes" and lower production costs

Active Publication Date: 2022-07-22
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, this method has not been reported in the literature, and it is highly innovative

Method used

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  • A kind of method for n-hydroxyphthalimide catalyzed electrolytic synthesis of fluorenone
  • A kind of method for n-hydroxyphthalimide catalyzed electrolytic synthesis of fluorenone
  • A kind of method for n-hydroxyphthalimide catalyzed electrolytic synthesis of fluorenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Electrochemical synthesis of fluorenone

[0032] In the single-chamber electrolytic cell, the raw materials o-phenylbenzohydrazide (0.3 mmol), N-hydroxyphthalimide (0.075 mmol, 25 mol%) and LiClO were added respectively. 4 (1 mmol) and 2,4,6-collidine (0.05 mmol, 17%). Using acetonitrile (5.0 mL) as solvent, the anode is graphite felt (1.0 × 1.0 cm) 2 ), the cathode is platinum mesh (1.0×1.0cm 2 ). The reaction was carried out by stirring and electrifying in a water bath at 50°C, and the voltage was 3V, and the progress of the reaction was detected by TLC. When TLC detects the disappearance of the raw material o-phenylbenzoic hydrazide, the electricity is stopped and the reaction is stopped. The reaction system was washed with DCM for the anode and cathode liquids into a 50 mL eggplant-shaped flask, and the DCM and the acetonitrile in the reaction solvent were removed by rotary evaporation under reduced pressure. The solid in the eggplant-shaped bottle w...

Embodiment 2

[0035] Example 2: Electrochemical synthesis of 2-fluorofluorenone

[0036] The raw materials 4-fluoro-1,1-biphenyl-2-carbohydrazide (0.3 mmol), N-hydroxyphthalimide (0.075 mmol, 25 mol%), and LiClO were respectively added to the single-chamber electrolytic cell. 4 (1 mmol) and 2,4,6-collidine (0.05 mmol, 17%). Using acetonitrile (5.0 mL) as solvent, the anode is graphite felt (1.0 × 1.0 cm) 2 ), the cathode is platinum mesh (1.0×1.0cm 2 ). The reaction was carried out by stirring and electrifying in a water bath at 50°C, and the voltage was 3V, and the progress of the reaction was detected by TLC. When TLC detects the disappearance of the raw material o-phenylbenzoic hydrazide, the electricity is stopped and the reaction is stopped. The reaction system was washed with DCM for the anode and cathode liquids into a 50 mL eggplant-shaped flask, and the DCM and the acetonitrile in the reaction solvent were removed by rotary evaporation under reduced pressure. The solid in the ...

Embodiment 3

[0039] Example 3: Electrochemical synthesis of 2-methylfluorenone

[0040] The raw materials 4-methyl-1,1-biphenyl-2 carboxylhydrazide (0.3mmol), N-hydroxyphthalimide (0.075mmol, 25mol%), LiClO were added to the single-chamber electrolytic cell, respectively. 4 (1 mmol) and 2,4,6-collidine (0.05 mmol, 17%). Using acetonitrile (5.0 mL) as solvent, the anode is graphite felt (1.0 × 1.0 cm) 2 ), the cathode is platinum mesh (1.0×1.0cm 2 ). The reaction was carried out by stirring and electrifying in a water bath at 50°C, and the voltage was 3V, and the progress of the reaction was detected by TLC. When TLC detects the disappearance of the raw material o-phenylbenzoic hydrazide, the electricity is stopped and the reaction is stopped. The reaction system was washed with DCM for the anode and cathode liquids into a 50 mL eggplant-shaped flask, and the DCM and the acetonitrile in the reaction solvent were removed by rotary evaporation under reduced pressure. The solid in the egg...

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Abstract

A method for catalyzing and electrolytically synthesizing fluorenone by N-hydroxyphthalimide belongs to the technical field of compound synthesis. Including the following experimental steps: respectively adding o-phenyl benzohydrazide compound (I) inside the single-chamber electrolytic cell, using N-hydroxyphthalimide as a catalyst, lithium perchlorate as a supporting electrolyte, 2, 4,5-trimethylpyridine as basic additive and under the condition that solvent exists, react 1-4 hours under constant pressure to obtain the fluorenone compound (II) shown below wherein, R 1 stands for -H, halogen, alkyl; R 2 Represents -H, halogen, alkyl.

Description

technical field [0001] The invention relates to a new method for using N-hydroxyphthalimide as an electrocatalyst to electrolyze benzohydrazide to generate fluorenone, and the strategy has not been reported in literature. Compared with the previous fluorenone synthesis method, the synthesis method protected by the present invention uses electrons as a clean oxidant, does not require expensive transition metal catalysts or photocatalysts, and does not require the participation of toxic and harmful chemical oxidants, and the by-products of the reaction are non-toxic. Therefore, this method has significant advantages of green and environmental protection. Background technique [0002] Fluorenone compounds widely exist in natural products and drug molecules. In recent years, drug molecules with fluorenone as the core structure have been continuously developed. For example, compound A has a very good anti-HIV activity; compound B is Tilorone, which is a broad-spectrum antiviral ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/09C25B3/07C25B3/05C25B3/11C25B3/23
CPCC25B3/09C25B3/07C25B3/05C25B3/11C25B3/23
Inventor 曾程初王婷张浩南徐坤
Owner BEIJING UNIV OF TECH
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