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6-aryloxy-7-chloro-4-hydroxy-3-quinolinecarboxylate synthesis and uses

A technology of ethyl quinoline carboxylate and aryloxy, which is applied in the field of synthesis of ethyl 6-aryloxy-7-chloro-4-hydroxy-3-quinoline carboxylate, can solve the problem of high compound price and influence Problems such as mass use of the product

Inactive Publication Date: 2007-07-11
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The synthesis of this type of compound requires a total of 8 steps, and the long synthetic route causes the price of the compound to be high, which affects the mass use of the product

Method used

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  • 6-aryloxy-7-chloro-4-hydroxy-3-quinolinecarboxylate synthesis and uses
  • 6-aryloxy-7-chloro-4-hydroxy-3-quinolinecarboxylate synthesis and uses
  • 6-aryloxy-7-chloro-4-hydroxy-3-quinolinecarboxylate synthesis and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: Preparation of target object 4a

[0025] (1) First add 13.66g (0.122mol) of p-fluorophenol in a 250ml three-necked bottle, heat and melt, then add 6.98g (0.122mol) of KOH, stir until all the generated water runs away, then add 19.3g ( 0.1 mol) of 1,2-dichloro-4-nitrobenzene, heated to an internal temperature of 150° C., reacted for 1 hour and 40 minutes, and detected the end point of the reaction by TLC. After the reaction, add 5% NaOH solution to the reaction system at 80°C to wash for 3 times, then wash with water twice at the same temperature, adjust the pH value to neutral with dilute HCl, pour the reaction solution into cold water while it is hot , cooled, suction filtered, and dried to obtain brown intermediate 1 with a yield of 84%.

[0026] (2) First add 22.50g (0.084mol) of intermediate 1 and 60ml of ethyl acetate into a 250ml round bottom flask, stir, and heat in a water bath until the external temperature is 40°C. After it is completely dissolv...

Embodiment 2

[0028] Embodiment 2: the preparation of target object 4b

[0029] Using p-bromophenol as raw material, the reaction steps are the same as above to obtain the target compound 4b.

Embodiment 3

[0030] Embodiment 3: the preparation of object 4c

[0031] Using p-methoxyphenol as raw material, the reaction steps are the same as above to obtain the target compound 4c.

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Abstract

The invention discloses a coccidiostat, which is characterized by the following: adopting substituted phenol-4-nitro-o-chlorobenzene as raw material; synthesizing 6-aryloxy-7-chloride-4-hydroxy-3-quinoline carboxylic ester.

Description

field of invention [0001] The invention relates to the synthesis and application of ethyl 6-aryloxy-7-chloro-4-hydroxyl-3-quinolinecarboxylate. Background of the invention [0002] Chicken coccidiosis is caused by 7 species of coccidia of Eimeriaceae and Eimeria genus parasitic in the digestive tract of chickens. It is one of the diseases that cause the greatest loss in intensive chicken farming. At present, the prevention and treatment of coccidiosis mainly depends on drugs, and systematically adding drugs to feed is a common method in the chicken industry. Due to the large amount of anticoccidial drugs used in the world, the area of ​​use is wide, and the application period is long, so far, coccidia can produce drug resistance to almost all drugs, and often show multi-drug resistance and cross-drug resistance. One of the solutions is to continuously develop new drugs. [0003] At present, benzyloxyquinate and decoquinate (compound 2, Chinese Journal of Veterinary Medicin...

Claims

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Application Information

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IPC IPC(8): C07D215/56A61K31/438A61P33/02
Inventor 杨祖幸陈华邹燕朱基美王玉良
Owner SICHUAN UNIV
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