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A method for synthesizing 2-acetyl-1,10-phenanthroline

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, low yield, etc., to improve purification efficiency, increase reactivity, and cost low effect

Active Publication Date: 2020-07-03
BEIJING YANLIAN CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The method for preparing 2-acetyl-1,10-phenanthroline comprises adding 1,10-phenanthroline and ethylene dichloride in a container at a mass ratio of 1:50, and then stirring the container under an ice-water bath , and add trifluoromethanesulfonic anhydride, the mass ratio of the addition of trifluoromethanesulfonic anhydride to 1,10-phenanthroline is 1:1, then the container is placed at room temperature and stirred for 1 hour, and trimethylsilyl cyanide is added , the mass ratio of the amount 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-diazabicyclodeca is added The mass ratio of one carbon-7-ene (DBU), 1,8-diazabicycloundec-7-ene (DBU) to 1,10-phenanthroline was 0.5:1, at 84 Stir at ℃ for 17 hours, cool the mixture to room temperature, quench with saturated sodium bicarbonate solution, extract with dichloromethane, and wash with saturated sodium chloride solution. Af...

Embodiment 2

[0026] Referring to Example 1, the method for preparing 2-acetyl-1,10-phenanthroline includes adding 1,10-phenanthroline and ethylene dichloride in a container at a mass ratio of 1:100, and then placing the container in Stir under ice-water bath, and add trifluoromethanesulfonic anhydride, the mass ratio of the addition of trifluoromethanesulfonic anhydride and 1,10-phenanthroline is 1: 4, then container is placed in room temperature and stirred 1 hour, adds Trimethylsilyl cyanide, the mass ratio of the amount of trimethylsilyl cyanide to 1,10-phenanthroline is 2:1, then the container is heated to 84°C, and stirring is continued for 4 hours, and finally 1,8-diphenanthroline is added The mass ratio of azabicycloundec-7-ene (DBU), 1,8-diazabicycloundec-7-ene (DBU) to 1,10-phenanthroline 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 saturated sodium c...

Embodiment 3

[0028]Referring to Example 1, the method for preparing 2-acetyl-1, 10-, phenanthroline includes adding 1, 10-phenanthroline and ethylene dichloride in a container at a mass ratio of 1:75, and then placing the container Stir in an ice-water bath, and add trifluoromethanesulfonic anhydride, the mass ratio of the amount of trifluoromethanesulfonic anhydride to 1,10-phenanthroline is 1:2, then the container is placed at room temperature and stirred for 1 hour, Add trimethylsilyl cyanide, the mass ratio of trimethylsilyl cyanide to 1,10-phenanthroline is 5:1, then raise the temperature of the container to 84°C, continue stirring for 4 hours, and finally add 1,8- The mass ratio of diazabicycloundec-7-ene (DBU), 1,8-diazabicycloundec-7-ene (DBU) to 1,10-phenanthroline 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 chloride solution, and extr...

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PUM

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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. 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 product is...

Claims

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Application Information

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