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
View PDF4 Cites 9 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing phenazine-1-carboxylic acid
  • Method for synthesizing phenazine-1-carboxylic acid
  • Method for synthesizing phenazine-1-carboxylic acid

Examples

Experimental program
Comparison scheme
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.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap