The preparation method of 7-chloro-8-quinoline carboxylic acid

A technology of quinoline carboxylic acid and methyl quinoline, which is applied in the field of herbicides, can solve a large number of waste acids and waste water, and achieve the effects of reducing the cost of three wastes treatment, low oxidation reaction temperature, and avoiding waste acid and waste water

Active Publication Date: 2021-06-08
NUTRICHEM LAB CO LTD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0007] The purpose of the present invention is to provide a new preparation method of 7-chloro-8-quinolinecarboxylic acid in order to overcome the problem of producing a large amount of waste acid and waste water in the synthetic process that prior art exists, and this method can avoid synthetic process The production of a large amount of waste acid and waste water in the middle of the process, and the reaction liquid phase can be recovered and applied mechanically

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  • The preparation method of 7-chloro-8-quinoline carboxylic acid
  • The preparation method of 7-chloro-8-quinoline carboxylic acid

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preparation example Construction

[0022] The invention provides a kind of preparation method of 7-chloro-8-quinoline carboxylic acid, the method comprises the following steps:

[0023] 1) In the reaction solution in which N-hydroxyphthalimide compounds and azobisisobutyronitrile are dissolved as catalysts, oxygen is used as an oxidant to oxidize 7-chloro-8-methylquinoline to obtain 7-Chloro-8-quinolinecarboxylic acid;

[0024] 2) separating the oxidation product from step 1) into solid and liquid to obtain a solid phase and a reaction liquid phase.

[0025] According to the method of the present invention, by using N-hydroxyphthalimide compounds and azobisisobutyronitrile as a catalyst, oxygen is used as an oxygenant to oxidize 7-chloro-8-methylquinoline, which can The generation of waste acid and waste water in the oxidation process is avoided, and high-purity 7-chloro-8-quinolinecarboxylic acid can be obtained with low reaction temperature and simple post-treatment.

[0026] In addition, by adopting the ab...

Embodiment 1

[0046] 1) In a 100 milliliter Hastelloy autoclave, add 10 grams of 7-chloro-8-methylquinoline, 40 milliliters of acetonitrile, 0.18 grams (0.02 equivalents) of N-hydroxyphthalimide, azobis Isobutyronitrile 0.093 grams (0.01 equivalent), closed autoclave, nitrogen replacement 2 times, oxygen replacement 3 times, oxygen pressurization 4MPa, be warming up to 80 ℃ of reaction 6 hours, the oxygen pressure in the reactor must not be lower than 4MPa in the reaction process. After the reaction, the temperature and pressure were lowered, and the reaction solution was filtered. The filter cake was slurried with 20 ml of acetonitrile, filtered, and the solid was dried to obtain 10.8 g of 7-chloro-8-quinolinecarboxylic acid, with a content of 98.2% by weight and a yield of 90.7%. After filtering the mother liquor, the corresponding 7-chloro-8-methylquinoline was added, and the reaction was continued.

[0047] 1 H-NMR(500MHz,d6-DMSO):δ13.645(s,1H),8.986-8.974(dd,1H,J 1 =1.5Hz,J 2 =2Hz),...

Embodiment 2

[0054] 1) In a 100 ml Hastelloy autoclave, add 10 grams of 7-chloro-8-methylquinoline, 40 milliliters of acetonitrile, 0.38 grams (0.04 equivalents) of N-hydroxyphthalimide, and azobis Isobutyronitrile 0.18 grams (0.02 equivalent), closed autoclave, nitrogen replacement 2 times, oxygen replacement 3 times, oxygen pressure 4MPa, be warming up to 90 ℃ of reaction 9 hours, the oxygen pressure in the reactor must not be lower than 4MPa in the reaction process. After the reaction was finished, the temperature and pressure were lowered, the reaction solution was filtered, and the filter cake was beaten with 30 milliliters of acetonitrile, filtered, and after the solid was dried, it was identified by NMR and mass spectrometry to obtain 11.1 grams of 7-chloro-8-quinoline carboxylic acid, with a content of 98.7% by weight. Yield 93.6%. After filtering the mother liquor, the corresponding 7-chloro-8-methylquinoline was added, and the reaction was continued.

[0055] 2) Apply mechanical...

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Abstract

The present invention relates to the field of herbicides, in particular to a preparation method of 7-chloro-8-quinoline carboxylic acid, the method comprising the following steps: 1) dissolving N-hydroxyphthalimides as a catalyst In the reaction liquid of compound and azobisisobutyronitrile, with oxygen as oxidant, 7-chloro-8-methylquinoline is oxidized to obtain 7-chloro-8-quinoline carboxylic acid; 2) the oxidation of step 1) The product is separated into solid and liquid to obtain a solid phase and a reaction liquid phase. Through the method of the invention, the production of a large amount of waste acid and waste water in the synthesis process can be avoided, and the reaction liquid phase can be recovered and used mechanically.

Description

technical field [0001] The invention relates to the field of herbicides, in particular to a preparation method of 7-chloro-8-quinoline carboxylic acid. Background technique [0002] Quinclorac, also known as 3,7-dichloro-8-quinoline carboxylic acid, is an effective selective herbicide for controlling barnyardgrass in rice fields, and belongs to the hormone-type quinolinic acid herbicide. 7-Chloro-8-quinoline carboxylic acid is an important intermediate compound for the preparation of 3,7-dichloro-8-quinoline carboxylic acid. Looking for a green, environmentally friendly, high-yield, and easy-to-operate oxidation method, the above-mentioned herbicides Industrialized production is of great significance. [0003] Patent application CN101851197A discloses a method for synthesizing and refining dichloroquinoline carboxylic acid, using m-chloro-o-toluidine and glycerol as raw materials to prepare 7-chloro-8-methylquinoline, and then 7-chloro-8-methylquinoline 3,7-dichloro-8-chlo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/48
CPCC07D215/48
Inventor 付裕王晓刚涂俊清路风奇张艳芳霍世勇
Owner NUTRICHEM LAB CO LTD
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