Method for synthesizing phenazine-1-carboxylic acid

A technology of carboxylic acid and methylphenazine, applied in the field of chemistry, can solve the problems of cumbersome processing, unsuitable for large-scale production, and expensive raw materials

Inactive Publication Date: 2014-09-17
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] In 2013, Li Yu et al. reported a synthetic method of Shenzimycin (CN103373967A) as shown below. This route is similar to the route two proposed by Rewcastle.Gordon W. The reaction conditions are harsh, and the price of raw materials is relatively expensive. Post-processing is cumbersome, so this route is not suitable for large-scale 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
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of 1-bromomethylphenazine (compound III)

[0027] Add (1.95g, 10.0mmol) compound IV in a 100mL four-necked flask, 20.0ml of carbon tetrachloride, N-bromosuccinimide (0.90g, 5mmol), benzoyl peroxide (0.39g, 1.6 mmol). The mixture was then heated to reflux, at which temperature N-bromosuccinimide (0.81 g, 5 mmol) was added portionwise. After the addition was complete, the reaction was carried out for 5 hours (TLC followed the reaction). The reaction mixture was poured into water (50.0 mL), and the obtained mixture was extracted with ethyl acetate (40.0 mL×3). After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain a yellow solid, which was finally subjected to silica gel column chromatography (petroleum Ether:ethyl acetate=30:1) isolated to obtain 1.02 g of compound III with a melting point of 163-165° C. and a yield of 40.0%.

Embodiment 2

[0028] Embodiment 2: the synthesis of 1-bromomethylphenazine (compound III)

[0029] Add (1.95g, 10.0mmol) compound IV in a 100mL four-necked flask, carbon tetrachloride 20.0ml, N-bromosuccinimide (1.21g, 6.5mmol), benzoyl peroxide (0.39g , 1.6 mmol). The mixture was then heated to reflux at which temperature N-bromosuccinimide (1.32 g, 6.5 mmol) was added portionwise. After the addition was complete, the reaction was carried out for 4 hours (TLC followed the reaction). The reaction mixture was poured into water (50.0 mL), and the obtained mixture was extracted with ethyl acetate (40.0 mL×3). After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain a yellow solid, which was finally subjected to silica gel column chromatography (petroleum Ether: ethyl acetate = 30:1) isolated to obtain 2.09 g of compound III with a melting point of 163-165° C. and a yield of 76.1%.

Embodiment 3

[0030] Embodiment 3: the synthesis of 1-bromomethylphenazine (compound III)

[0031] Add (1.95g, 10.0mmol) compound IV in a 100mL four-necked flask, carbon tetrachloride 20.0mL, N-bromosuccinimide (1.35g, 7.5mmol), benzoyl peroxide (0.39g , 1.6 mmol). The mixture was then heated to reflux at which temperature N-bromosuccinimide (1.35 g, 7.5 mmol) was added portionwise. After the addition was complete, the reaction was carried out for 3.5 hours (TLC followed the reaction). The reaction mixture was poured into water (50.0 mL), and the obtained mixture was extracted with ethyl acetate (40.0 mL×3). After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain a yellow solid, which was finally subjected to silica gel column chromatography (petroleum Ether:ethyl acetate=30:1) isolated to obtain 2.48g of compound III with a melting point of 163-165°C and a yield of 91.0%.

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Abstract

The invention provides a method for synthesizing phenazine-1-carboxylic acid. The method comprises the steps of carrying out bromination reaction on 1-methyl-phenazine as a starting material and N-bromosuccinimide in the presence of benzoyl peroxide as a catalyst to produce 1-bromomethylphenazine, further hydrolyzing 1-brominemethylphenazine to obtain 1-hydroxymethyl phenazine and finally oxidizing to obtain phenazine-1-carboxylic acid, namely, shenqinmycin. According to the method disclosed by the invention, disadvantages of low yield, relatively high production cost, high treatment cost of three wastes and the like are solved, and the method for synthesizing phenazine-1-carboxylic acid with the advantages of simple synthetic steps, high yield, low cost and environment friendliness is provided.

Description

technical field [0001] The invention belongs to the organic synthesis of green microbial source pesticides and their intermediates in the chemical field, and in particular relates to a method for synthesizing phenazine-1-carboxylic acid. technical background [0002] In 1997, the research team of Professor Xu Yuquan of Shanghai Jiaotong University isolated a Pseudomonas fluorescens strain M18 with high-efficiency and broad-spectrum antibacterial effect on various plant pathogens from the soil around the melon rhizosphere (this strain has obtained a national invention patent, Patent No.: ZL0011985712). Further scientific research, the main bactericidal active substance was extracted and determined from the fermentation broth of Pseudomonas fluorescens strain M18. The carboxylic acid has the same physical and chemical properties and biological activity as the chemically synthesized phenazine-1-carboxylic acid. [0003] [0004] Shenzimycin is a biological fungicide with p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/46
CPCC07D241/46
Inventor 朱红军展秋英朱晓林何广科宋广亮刘睿刘琪
Owner NANJING TECH UNIV
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