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Method for preparing ketone nitrile by using metalloporphyrin polymer for catalytic coupling of aromatic alcohol and acetonitrile

A metalloporphyrin, aromatic alcohol technology, applied in the direction of organic compound/hydride/coordination complex catalyst, organic compound preparation, physical/chemical process catalyst, etc.

Inactive Publication Date: 2018-11-16
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods have disadvantages such as the need for strong bases or highly toxic cyanide

Method used

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  • Method for preparing ketone nitrile by using metalloporphyrin polymer for catalytic coupling of aromatic alcohol and acetonitrile
  • Method for preparing ketone nitrile by using metalloporphyrin polymer for catalytic coupling of aromatic alcohol and acetonitrile
  • Method for preparing ketone nitrile by using metalloporphyrin polymer for catalytic coupling of aromatic alcohol and acetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] 10mg of the metalloporphyrin polymer with the structure of structural formula (I), M=Cu(II), m=382, specific surface area 730m 2 / g. Benzyl alcohol (1mmol, 0.108g), acetonitrile (5mmol, 0.206g), KOH (3mmol, 0.168g) were added to 10mL of N,N-dimethylformamide, and 50mL / min of air was blown. The reaction was stirred at 60°C for 5 hours, the corresponding yield of ketone nitrile was 93%, and the conversion of benzyl alcohol was 92%.

Embodiment 2

[0014] 10mg of the metalloporphyrin polymer with the structure of structural formula (I), M=Zn(II), m=510, specific surface area 680m 2 / g. P-Nitrobenzyl alcohol (1mmol, 0.153g), acetonitrile (10mmol, 0.411g), KOH (3mmol, 0.168g) were added to 10mL of dimethyl sulfoxide, and 50mL / min of air was introduced. The reaction was stirred at 80°C for 3 hours. The yield of the corresponding ketonitrile was 90% and the conversion rate of p-nitrobenzyl alcohol was 91%.

Embodiment 3

[0016] 10mg of the metalloporphyrin polymer with the structure of structural formula (I), M=Co(II), m=280, specific surface area 850m 2 / g. P-methylbenzyl alcohol (1mmol, 0.122g), acetonitrile (10mmol, 0.411g), t-BuOK (3mmol, 0.336g), added to 10mL of 1,3-dimethyl-2-imidazolinone, through Into 50mL / min air. The reaction was stirred at 50°C for 8 hours, the corresponding ketonitrile yield was 91%, and the p-methylbenzyl alcohol conversion rate was 90%.

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Abstract

The invention discloses a method for preparing ketone nitrile by using a metalloporphyrin polymer for catalytic coupling of aromatic alcohol and acetonitrile. The porous polymeric metalloporphyrin having a high poriform structure and a specific surface area and connected by a nitrogen-containing bridge bond and containing 2 coordination metal ions is selected as a catalyst, and aromatic alcohol and acetonitrile are subjected to catalytic oxidation coupling under mild condition to obtain the corresponding ketone nitrile product. The catalyst amount is less, and the catalysis effect is good. Thecatalyst is un-dissolved and un-decomposed in a reaction system, multitime cycle usage is realized, a reaction conversion rate is high, and the selectivity is good.

Description

Technical field [0001] The invention relates to a method for preparing ketone nitrile by catalytic oxidative coupling of aromatic alcohol compounds under mild conditions. Background technique [0002] Ketone nitrile is a very useful synthetic intermediate. They have been used as precursors of various heterocyclic structures, including aminopyrazole, aminoisoxazole, 2-pyridone and imidazole. In addition, they have been used to synthesize a variety of pharmacologically active compounds, such as anti-HCV drugs and anti-NHE-1 inhibitors. Common methods for preparing β-keto nitrile include the coupling of alkyl nitrile and ester in the presence of a strong base or the cyanide displacement reaction with α-bromoketone. These methods have disadvantages such as the need for strong bases or highly toxic cyanide. For example, patents US6822110 and CN102020586A both use a highly toxic and lethal hydrocyanic acid solution. Therefore, it is very necessary to develop a low-toxic, high-effic...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/40B01J31/22
CPCC07C253/30B01J31/1691B01J31/183B01J2231/70B01J2231/4205B01J2531/845B01J2531/26B01J2531/16B01J2531/025B01J35/617B01J35/647B01J35/615C07C255/40Y02P20/584
Inventor 阳卫军柳恩情高勇
Owner HUNAN UNIV
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