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Method for synthesizing phenazine-1-carboxylic acid

A certain amount of shenzimycin, which is applied in the field of synthesis of the microbial-derived pesticide shenzimycin, can solve the problems of harsh conditions, unsuitability for industrial production, and low yield in the second step.

Inactive Publication Date: 2013-09-18
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In the second step of route 2, the yield is relatively low, the conditions are harsh, and it is not suitable for industrial production

Method used

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  • Method for synthesizing phenazine-1-carboxylic acid
  • Method for synthesizing phenazine-1-carboxylic acid
  • Method for synthesizing phenazine-1-carboxylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of 1-methyl-5,10-dihydrophenazine

[0032] In the glove box of nitrogen atmosphere, weigh catechol (1.1g, 10mmol), 2,3-diaminotoluene (1.22g, 10mmol), then pour into mortar, grind and mix well, transfer the mixture to In a 50ml four-neck flask, under magnetic stirring, heat up to 210°C, melt, and keep warm for 35h. Cool to below 100°C, add hot water, stir for about 2 hours, and filter with suction. The filter cake was washed several times with 80°C water and dried to obtain a yellow-green solid. Petroleum ether was recrystallized to obtain 1.26 g of pale yellow-green crystals. Yield 64.2%, melting point 181-182°C.

Embodiment 2

[0033] Embodiment 2: the preparation of 1-methyl-5,10-dihydrophenazine

[0034] In the glove box of nitrogen atmosphere, take catechol (1.32g, 12mmol), 2,3-diaminotoluene (1.22g, 10mmol), then pour into mortar, fully grind and mix, and transfer the mixture to In a 50ml four-neck flask, under magnetic stirring, heat up to 190°C, melt, and keep warm for 40h. Cool to below 100°C, add hot water, stir for about 2 hours, and filter with suction. The filter cake was washed several times with 80°C water and dried to obtain a yellow-green solid. Petroleum ether was recrystallized to obtain 1.43 g of light yellow-green crystals. Yield 73.1%, melting point 181-182°C.

Embodiment 3

[0035] Embodiment 3: the preparation of 1-methyl-5,10-dihydrophenazine

[0036] In a glove box under a nitrogen atmosphere, weigh catechol (1.1g, 10mmol), 2,3-diaminotoluene (1.46g, 12mmol), pour into a mortar, grind and mix well, and transfer the mixture to In a 50ml four-neck flask, under magnetic stirring, heat up to 150°C, melt, and keep warm for 50h. Cool to below 100°C, add hot water, stir for about 2 hours, and filter with suction. The filter cake was washed several times with 80°C water and dried to obtain a yellow-green solid. Petroleum ether was recrystallized to obtain 1.31 g of pale yellow-green crystals, with a yield of 66.9% and a melting point of 181-182°C.

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Abstract

The invention provides a method for synthesizing phenazine-1-carboxylic acid. The method comprises the following steps: dehydrating initial raw materials comprising catechol and 2,3-diaminotoluene in the nitrogen atmosphere, carrying out a cyclization reaction to generate 1-methy-5,10-dihydrophenazine, reacting with air for an oxidation reaction to obtain 1-methylphenazine, chlorinating 1-methylphenazine by chlorine under the catalysis of azodiisobutyronitrile, and hydrolyzing to obtain phenazine-1-carboxylic acid. The method solves the disadvantages of low efficiency, high cost, large wastewater amount and the like of previous production methods through biological fermentation, and is a new phenazine-1-carboxylic acid production technology having the advantages of high efficiency, low cost and environmental protection.

Description

technical field [0001] The invention relates to a method for synthesizing microbial source pesticide shenzamycin, in particular to a method for synthesizing phenazine-1-carboxylic acid. When synthesizing phenazine-1-carboxylic acid, it specifically involves ring formation, oxidation, substitution, and hydrolysis reactions. technical background [0002] In 1996, researchers from the School of Life Science and Technology of Shanghai Jiao Tong University started research on biopesticides. In 1997, Shanghai Jiaotong University isolated a Pseudomonas fluorescens strain M18 with a strong broad-spectrum antibacterial effect on a variety of plant pathogens from the soil around the melon rhizosphere in the suburbs of Shanghai (this strain has obtained a national invention patent, patent No.: ZL 0011985712). [0003] Further studies have found that the main active ingredient of the growth-promoting antagonistic bacteria M18 in preventing and controlling plant diseases is phenazine-1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/46
Inventor 朱红军朱晓林何广科宋广亮黄仁钧施路
Owner NANJING UNIV OF TECH
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