Method for preparing 8-quinoline carboxylic acid and derivatives of 8-quinoline carboxylic acid

A technology for quinoline carboxylic acid and derivatives, which is applied in the field of catalytic oxidation of quinoline derivatives to prepare 8-quinoline carboxylic acid and its derivatives, which can solve the problems of reducing production costs and achieve low production costs and high process safety , the effect of improving the reaction efficiency

Active Publication Date: 2021-01-05
JIANGSU KUAIDA AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The invention adopts high-efficiency Cu-Co-X ternary composite catalyst, reacts at 50-150°C under normal pressure, the reaction conditions are mild, the oxidation yield is significantly improved, the three wastes are realized near zero discharge, the pollution problem is effectively solved, and the pollution is greatly reduced. cost of production

Method used

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  • Method for preparing 8-quinoline carboxylic acid and derivatives of 8-quinoline carboxylic acid
  • Method for preparing 8-quinoline carboxylic acid and derivatives of 8-quinoline carboxylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0017] In a 2L four-neck flask, add 150 g of 8-chloromethylquinoline, CoCl 2 ·6H 2 O 0.5g, AgCl 0.6g, CuCl 0.2g, acetonitrile-water (volume ratio 1:1) 800mL, start stirring, heat to reflux, start to feed oxygen slowly, the oxygen flow rate is 50mL / min, the reaction time is about 8h, stop feeding oxygen; distill under reduced pressure, evaporate at -0.095Mpa to a temperature of 90°C, cool down to room temperature in a water bath, add 150ml of water, stir well, filter, and distill the filtrate under reduced pressure to obtain a solid catalyst, which is recovered and used mechanically; 139.3 g of 8-quinolinic acid was obtained by drying, the content was 86%, and the yield was 81.5%.

Embodiment 2

[0019] In the 2L four-necked flask, add 8-methylquinoline 150g successively, Co(NO 3 ) 2 ·6H 2 O 0.4g, FeSO 4 0.8g, Cu(NO 3 ) 2 0.4g, 2-Methyltetrahydrofuran-water (volume ratio 2:1) 800mL, start stirring, heat to reflux, start to slowly pass in ozone, the flow rate of oxygen is 30mL / min, the reaction time is about 6.5h, stop the flow into ozone; vacuum distillation, -0.095Mpa steamed down to a temperature of 80°C, cooled to room temperature in a water bath, added 150ml of water, fully stirred, filtered, and the filtrate was distilled under reduced pressure to obtain a solid catalyst, which was recovered and used mechanically; the filter cake was dried to obtain 8- Quinolinic acid 144.6g, content 90%, yield 88.5%.

Embodiment 3

[0021] In a 2L four-neck flask, add 3,7-dichloro-8-chloromethylquinoline 150g, Co(OAc) 2 4H 2 O 0.2g, Na 2 WO 4 2H 2 O 0.5g, Cu(OAc) 2 ·H 2 O 0.5g, 800mL of chlorobenzene, start stirring, heat to 110°C, start to introduce ozone slowly, the flow rate of oxygen to be introduced is 25mL / min, the reaction time is about 8h, stop introducing ozone; distill under reduced pressure, cool to room temperature in water bath , filtered, and the filtrate was distilled under reduced pressure to obtain a solid catalyst, which was recovered and used mechanically; the filter cake was dried to obtain 117.2 g of 3,7-dichloro-8-quinolinic acid, with a content of 92% and a yield of 90.8%.

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Abstract

The invention discloses a method for preparing 8-quinoline carboxylic acid and derivatives thereof, which comprises the following steps: by using a compound I as a raw material, reacting with an oxidant at the temperature of 50-150 DEG C under normal pressure in a solvent under the action of a Cu-Co-X ternary composite catalyst to obtain a compound II; according to the method, the efficient Cu-Co-X ternary composite catalyst is adopted, the reaction is carried out at the temperature of 50-150 DEG C under normal pressure, the reaction condition is mild, the oxidation yield is remarkably increased, near-zero emission of three wastes is realized, the pollution problem is effectively solved, and the production cost is greatly reduced.

Description

technical field [0001] The invention belongs to the field of organic chemical industry, and in particular relates to a method for preparing 8-quinolinecarboxylic acid and its derivatives by catalytically oxidizing quinoline derivatives. Background technique [0002] Quinoline derivatives are an important fine chemical raw material, and many compounds containing quinoline ring structures have shown wide application and development prospects. Among them, quinolinic acid is an important pesticide, medicine and pharmaceutical intermediate, and many quinoline derivatives are important pesticide varieties, such as 7-chloroquinoline N-oxide can be used as a herbicide for broad-leaved weeds in grain planting; Substituted 8-aminoquinolines have phytotoxic activity and can be used to prepare herbicides; herbicides can be prepared from quinoline esters of N-substituted disulfide carbamic acids, with low toxicity and residue; 2,3-quinoline dicarboxylic acid It is an intermediate of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/48
CPCC07D215/48Y02P20/584
Inventor 李炜钱圣利许雪飞常逸凡陆丹丹吴春辉
Owner JIANGSU KUAIDA AGROCHEM
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