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Method for synthesizing 2-acetyl-1, 10-phenanthroline (3)

A technology of phenanthroline and acetyl, which is applied in the field of synthesizing 2-acetyl-1, can solve the problems of low reaction selectivity, large consumption of hydrochloric acid, difficult separation, etc., to improve purification efficiency, increase reactivity, and low cost Effect

Active Publication Date: 2019-07-12
BEIJING YANLIAN CHEM TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] The synthesis of 2-acetyl-1,10-phenanthroline is generally obtained by reacting 8-aminoquinoline with pent-2-enal under the action of concentrated hydrochloric acid to obtain 2-ethyl-1,10-phenanthroline and then passing Oxidation to obtain 2-acetyl-1,10-phenanthroline, this reaction process consumes a large amount of hydrochloric acid, which puts great demands on the reaction equipment, and at the same time a large amount of waste acid needs to be treated, and the yield is generally not high
[0003] In addition, the target product can also be obtained from 1,10-phenanthroline as a starting agent by side chain alkylation. Because its reaction selectivity is not high, the unilaterally substituted alkylated phenanthroline product to be obtained , the yield is very low, the product is complex and difficult to separate

Method used

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  • Method for synthesizing 2-acetyl-1, 10-phenanthroline (3)

Examples

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Effect test

Embodiment 1

[0024] The method for preparing 2-acetyl-1,10-phenanthroline (3), comprising adding 1,10-phenanthroline and dichloroethane to a container at a mass ratio of 1:50, and then placing the container in an ice-water bath Under stirring, and add trifluoromethanesulfonic anhydride, the mass ratio of the addition amount of trifluoromethanesulfonic anhydride and 1,10-phenanthroline is 1:1, then the container is placed at room temperature and stirred for 1 hour, and trimethylsulfonic acid is added Cyanosilane, the mass ratio of trimethylsilyl cyanide to 1,10-phenanthroline is 4:1, then the container is heated to 84°C, and stirring is continued for 4 hours, and finally 1,8-diazepine is added Dicycloundec-7-ene (DBU), the mass ratio of 1,8-diazabicycloundec-7-ene (DBU) to 1,10-phenanthroline is 0.5:1 , stirred at 84°C for 17 hours, cooled the mixture to room temperature, quenched with saturated sodium bicarbonate solution, extracted with dichloromethane, washed with saturated sodium chlori...

Embodiment 2

[0026] Referring to Example 1, the method for preparing 2-acetyl-1,10-phenanthroline (3) includes adding 1,10-phenanthroline and dichloroethane to the container at a mass ratio of 1:100, and then The container was placed in an ice-water bath and stirred, and trifluoromethanesulfonic anhydride was added, and the mass ratio of the amount of trifluoromethanesulfonic anhydride to 1,10-phenanthroline was 1: 4, and then the container was stirred at room temperature for 1 hour, add trimethylsilyl cyanide, the mass ratio of the amount of trimethylsilyl cyanide to 1,10-phenanthroline is 2:1, then the container is warmed up to 84 ° C, continue to stir for 4 hours, and finally add 1, The amount of 8-diazabicycloundec-7-ene (DBU), 1,8-diazabicycloundec-7-ene (DBU) and the quality of 1,10-phenanthroline The ratio is 3:1, stirred at 84°C for 17 hours, cooled the mixture to room temperature, quenched with saturated sodium bicarbonate solution, extracted with dichloromethane, washed with satu...

Embodiment 3

[0028]Reference Example 1, the method for preparing 2-acetyl-1, 10-, phenanthroline (3), including adding 1, 10-phenanthroline and dichloroethane to the container at a mass ratio of 1:75, and then Place the container under an ice-water bath for stirring, and add trifluoromethanesulfonic anhydride, the mass ratio of the amount of trifluoromethanesulfonic anhydride to 1,10-phenanthroline is 1:2, and then place the container at room temperature to stir For 1 hour, add trimethylsilyl cyanide, the mass ratio of the amount of trimethylsilyl cyanide to 1,10-phenanthroline is 5:1, then the container is heated to 84°C, and stirring is continued for 4 hours, and finally 1 , 8-diazabicycloundec-7-ene (DBU), the amount of 1,8-diazabicycloundec-7-ene (DBU) and 1,10-phenanthroline The mass ratio is 2:1, stirred at 84°C for 17 hours, cooled the mixture to room temperature, quenched with saturated sodium bicarbonate solution, extracted with dichloromethane, washed with saturated sodium chlori...

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Abstract

The invention discloses a method for synthesizing 2-acetyl-1, 10-phenanthroline (3). The method comprises the following steps: using 1, 10-phenanthroline as a raw material to synthesize 2-cyano-1, 10-phenanthroline (2) by reacting with trimethylcyanosilane, trifluoromethanesulfonic anhydride, 1, 8-diazabicycloundec-7-ene; and then reacting 2-cyano-1, 10-phenanthroline (2) with methyl lithium to prepare 2-acetyl-1, 10-phenanthroline (3). The method provided by the invention prepares 2-acetyl-1, 10-phenanthroline (3) by adopting a two-step synthesis method, is beneficial to the increase of the yield, and purifies by quenching with a saturated sodium bicarbonate solution, extracting with dichloromethane and washing with a saturated sodium chloride solution after completing a first step, so that the influence of impurities generated in the first step on the reaction in a second step is minimized.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a method for synthesizing 2-acetyl-1,10-phenanthroline (3). Background technique [0002] The synthesis of 2-acetyl-1,10-phenanthroline is generally obtained by reacting 8-aminoquinoline with pent-2-enal under the action of concentrated hydrochloric acid to obtain 2-ethyl-1,10-phenanthroline and then passing Oxidation produces 2-acetyl-1,10-phenanthroline. This reaction process consumes a large amount of hydrochloric acid, which puts great demands on the reaction equipment. At the same time, a large amount of waste acid needs to be treated, and the yield is generally not high. [0003] In addition, the target product can also be obtained from 1,10-phenanthroline as a starting agent by side chain alkylation. Because its reaction selectivity is not high, the unilaterally substituted alkylated phenanthroline product to be obtained , the yield is very low, and the produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 沈阳
Owner BEIJING YANLIAN CHEM TECH CO LTD
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