Preparation method for phenazine-1-carboxylic acid

A technology of carboxylic acid and phenazine, which is applied in the field of preparation of active components of pesticides, can solve the problems of large investment in equipment, long reaction steps, and difficult availability of raw materials, etc., and achieve easy-to-obtain reaction raw materials, mild reaction conditions, and easy post-processing Effect

Active Publication Date: 2015-08-12
SHANGHAI TAIHE INT TRADE CO LTD +1
View PDF5 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the preparation of phenazine-1-carboxylic acid by biological fermentation faces the problems of large investment in equipment, low production efficiency, and high cost. In addition, the existing synthetic meth

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
  • Preparation method for phenazine-1-carboxylic acid
  • Preparation method for phenazine-1-carboxylic acid
  • Preparation method for phenazine-1-carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of α-oximinoacetanilide

[0040] Add 30g of chloral hydrate, 70g of hydroxylamine hydrochloride, 22g of anhydrous sodium sulfate, and 800g of water into a 1000mL four-necked bottle in sequence, and heat to 65°C. The suspension (20 g of 2-nitroaniline, 20 mL of 2N hydrochloric acid) was added. Insulation reaction 20h. Cool down to 5-8°C and keep warm for 2h. Filtration gave a yellow solid. After drying, 25 g of the title compound was obtained.

[0041] Preparation of isatin

[0042] Add 137g of concentrated sulfuric acid into a 100mL three-necked flask and heat to 80°C. Add 25 g of α-oximinoacetanilide several times, and control the temperature not to exceed 90°C. After the addition was complete, the reaction was incubated at 90°C for 2h. After cooling down to room temperature, the reaction solution was poured into about 300 g of ice to quench the reaction. Insulate at 5°C for 2 hours, and filter to obtain a khaki product. After drying, 24 g of the t...

Embodiment 2

[0054] A method for preparing phenazine-1-carboxylic acid, using the following steps:

[0055] (1) Synthesis of 2-bromo-3 nitrobenzoic acid

[0056] The reaction of aniline with chloral hydrate and hydroxylamine produces α-oximinoacetanilide, which is then treated with concentrated sulfuric acid to obtain isatin, which is reacted with hydrogen peroxide to obtain 2-amino-3-nitrobenzoic acid, which is then subjected to Sandmeyer reaction to obtain 2-bromo -3 nitrobenzoic acid, specifically adopt the following steps:

[0057] Mix chloral hydrate, hydroxylamine hydrochloride, and anhydrous sodium sulfate in a weight ratio of 30:80:30 and dissolve them in water, heat to 65°C, add 2-nitroaniline suspension, 2-nitroaniline The weight ratio to chloral hydrate is 30:30, keep the temperature down to 5-8°C after 20 hours of heat preservation, keep heat for 2 hours, and filter to obtain a yellow solid that is α-oximinoacetanilide.

[0058] The prepared α-oximino acetanilide was mixed wi...

Embodiment 3

[0067] A method for preparing phenazine-1-carboxylic acid, using the following steps:

[0068] (1) Synthesis of 2-bromo-3 nitrobenzoic acid

[0069] The reaction of aniline with chloral hydrate and hydroxylamine produces α-oximinoacetanilide, which is then treated with concentrated sulfuric acid to obtain isatin, which is reacted with hydrogen peroxide to obtain 2-amino-3-nitrobenzoic acid, which is then subjected to Sandmeyer reaction to obtain 2-bromo -3 Nitrobenzoic acid. Specifically take the following steps:

[0070] Mix chloral hydrate, hydroxylamine hydrochloride, and anhydrous sodium sulfate in a weight ratio of 20:60:20 and dissolve them in water, heat to 65°C, add 2-nitroaniline suspension, 2-nitroaniline The weight ratio to chloral hydrate is 20:20, heat preservation reaction for 20 hours, then cool down to 5°C, heat preservation for 2 hours, and filter to obtain a yellow solid which is α-oximinoacetanilide;

[0071] The prepared α-oximino acetanilide was mixed w...

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

No PUM Login to view more

Abstract

The invention relates to a preparation method for phenazine-1-carboxylic acid. The preparation method comprises the following steps: reacting aniline with chloral hydrate and hydroxylamine to produce alpha-oximidoacetanilide, treaing alpha-oximidoacetanilide with concentrated sulfuric acid to obtain isatin, reacting isatin with hydrogen peroxide so as to obtain 2-amino-3-nitrobenzoic acid and then carrying out Sandmeyer reaction to prepare 2-bromo-3-nitrobenzoic acid; and subjecting prepared 2-bromo-3-nitrobenzoic acid and aniline to Jourdan-Ullmann reaction so as to obtain substituted diphenylamine and carrying out ring closure to prepare phenazine-1-carboxylic acid. Compared with the prior art, the preparation method provided by the invention has the advantages of easy availability of raw materials, easy control of reaction, mild reaction conditions, easy post-treatment, high overall yield, as high as 32 to 47%, and suitability for industrial production; and compared with conventional method for production of shenqinmycin from ferment powder, the method provided by the invention enables cost to be greatly reduced.

Description

technical field [0001] The invention relates to a method for preparing pesticide active components, in particular to a method for preparing phenazine-1-carboxylic acid with antifungal activity. Background technique [0002] Phenazine-1-carboxylic acid is a broad-spectrum crop pathogenic fungal inhibitor produced by Jiaotong University through biological fermentation. It is the active ingredient of pesticide preparations against melons, fruits, vegetables and crop diseases and insect pests, and the active ingredient of pesticide preparations for rice sheath blight. [0003] J.Agric.Food Chem.2010,58,365 1-3660; J.Med.Chem., 2000,43,1350; J.Med.Chem., 1987,30,843. Reported by aniline and 2-bromo -3-Nitrobenzoic acid undergoes Jourdan-Ullmann reaction to obtain substituted diphenylamine, and then ring-closes to obtain phenazine-1-carboxylic acid. The raw material 2-bromo-3 nitrobenzoic acid used in this method is expensive and difficult to obtain. J.Org.Chem., 1955, 20, 797 r...

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
IPC IPC(8): C07D241/46
CPCC07D241/46
Inventor 李宗成季秀芳谢思勉田晓宏
Owner SHANGHAI TAIHE INT TRADE CO LTD
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