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Synthesis and application of 6-(2-methoxy phenoxy)-1,4-dihydrogen-4-oxo-3-ethyl quinolinecarboxylate

A technology of ethyl quinolinecarboxylate and methoxyphenoxy, which is applied in the directions of active ingredients of heterocyclic compounds, drug combinations, anti-infective drugs, etc., can solve the problems of high compound prices and affecting the mass use of products, etc.

Inactive Publication Date: 2007-01-24
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] It can be seen from the reaction formula 1 that 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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  • Synthesis and application of 6-(2-methoxy phenoxy)-1,4-dihydrogen-4-oxo-3-ethyl quinolinecarboxylate
  • Synthesis and application of 6-(2-methoxy phenoxy)-1,4-dihydrogen-4-oxo-3-ethyl quinolinecarboxylate
  • Synthesis and application of 6-(2-methoxy phenoxy)-1,4-dihydrogen-4-oxo-3-ethyl quinolinecarboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the preparation of intermediate 1

[0027] (1) First add 16.31g (0.13mol) of o-methoxyphenol into a 250ml three-necked bottle, heat and melt, then add 7.37g (0.13mol) of KOH, stir until all the generated water runs away, then add 18.91 g (0.12mol) of p-chloronitrobenzene, then heated to 150°C, and TLC measured the end point of the reaction. After the reaction, add 5% NaOH solution to the reaction system at 100°C to wash for 3 times, then wash with water at the same temperature until the pH value is neutral, then pour into cold water to cool, filter, and dry to obtain a yellow intermediate 1 25.6 g, yield 87%.

[0028] (2) First add 16.31g (0.13mol) of o-methoxyphenol into a 250ml three-necked bottle, heat and melt, then add 7.37g (0.13mol) of KOH, stir until all the generated water runs away, then add 18.91 g (0.12mol) of p-chloronitrobenzene, and then heated to 120° C., and TLC detected the end point of the reaction. After the reaction, first add 5% Na...

Embodiment 2

[0029] Embodiment 2: the preparation of intermediate 2 and intermediate 3

[0030] (1) First add 21.78g (0.0888mol) of intermediate 1 and 100ml of ethyl acetate into a 250ml three-necked flask, and raise the external temperature to 40°C. After it is completely dissolved, add 5.5g of Pd / C, and then introduce H 2 It takes about 4.5 hours until the reaction system stops absorbing. After the reaction, filter, add 19.19g (0.0888mol) diethyl ethoxymethylenemalonate to the filtrate immediately, heat to reflux, and react for 4.5 hours. The end point of the reaction was detected by TLC. After the reaction, the ethyl acetate was distilled off under reduced pressure, and then recrystallized with absolute ethanol to obtain a light yellow solid, which was dried to obtain 27.78 g of yellow intermediate 3 with a yield of 78%.

[0031] (2) First add 21.78g (0.0888mol) of intermediate 1 and 100ml of ethyl acetate into a 250ml three-necked flask, and raise the external temperature to 20°C. Aft...

Embodiment 3

[0032] Embodiment 3: the preparation of target object

[0033] (1) First add 100ml of diphenyl ether into a 250ml three-necked bottle, and when the temperature is raised to 250°C, add 20g of intermediate 3 and react for 2h. After the reaction, cool down, add 100ml of petroleum ether, filter, and dry to obtain 15.5g of the brown-yellow target substance, with a yield of 92%.

[0034] (2) First add 100ml of diphenyl ether into a 250ml three-necked bottle, and when the temperature is raised to 220°C, add 20g of intermediate 3 and react for 4h. After the reaction, cool down, add 100ml of petroleum ether, filter, and dry to obtain 11.84g of the brown-yellow target substance, with a yield of 70%.

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Abstract

The compound 6-(2-methoxy phenoxy)-1, 4-dihydrogen-4-oxo-3-ethyl quinoline carboxylate is prepared with o-methoxyphenol and p-chloronitrobenzene as materials and through four-step reaction. The coccidian antagonist experiment on chicken shows its coccidian antagonizing effect, and compared with available coccidian antagonist medicine, the compound of the present invention has the advantages of short synthesis path, high yield, low cost, etc.

Description

field of invention [0001] The invention relates to the synthesis and application of ethyl 6-(2-methoxyphenoxy)-1,4-dihydro-4-oxo-3-quinolinecarboxylate. Background of the invention [0002] Chicken coccidiosis is caused by seven species of coccidiosis of Eimeriaceae and Eimeria genus parasitic in the digestive tract of chickens. It is currently one of the diseases that cause the greatest loss in the chicken industry, especially in the intensive chicken industry. . In 1992 Bhogal estimated the loss at US$ 2 billion (Feed Research, 2003, NO 05, 36). 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 t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/56A61K31/47A61P33/00
Inventor 王玉良邹燕吴凯群刘庆辉朱基美
Owner SICHUAN UNIV
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