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Synthetic method of quinoxaline-2-ethyl-3-methyl-N1-oxide

A synthesis method and oxide technology, which are applied in the synthesis field of quinoxaline-2-ethyl-3-methyl-N1-oxide, can solve problems such as few literature reports, and achieve concise synthesis steps, easy realization, The effect of high product purity

Inactive Publication Date: 2013-05-01
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no synthetic patent of quinoxaline-2-ethyl-3-methyl-N1-oxide at home and abroad, and there are few literature reports. In order to make up for this gap, and further confirm its generation, and study its toxic and side effects , It is very important to prepare quinoxaline-2-ethyl-3-methyl-N1-oxide by chemical synthesis method for comparison, and the quinoxaline-2-ethyl-3-methyl-N1-oxide Chemical synthesis can not only provide standard products for the residue and metabolism research of such drugs, but also provide reference methods for similar metabolites

Method used

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  • Synthetic method of quinoxaline-2-ethyl-3-methyl-N1-oxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Quinoxaline-2-ethyl-3-methyl-N1, N4-dioxide

[0024] Add benzofurazan (26.3g), K2CO3 (50g), CH2Cl2 (200ml) to 2-pentanone (17g), drip n-butylamine (28.22g) within 1 hour at 30°C under stirring, and continue stirring for 5 hours. K2CO3 was filtered off, concentrated by distillation under reduced pressure, isopropanol was added, and the precipitate was deposited in ice water. After filtration, 4 g of yellow solid containing a small amount of benzofurazan was obtained, and 33.8 g of yellow needle-like crystals were obtained by recrystallization from ethanol several times. This reaction system will explode when the temperature exceeds 60°C.

[0025] (2) Quinoxaline-2-ethyl-3-methyl-N1-oxide

[0026] Weigh 1g of quinoxaline-2-ethyl-3-methyl-N1, N4-dioxide, add 30ml of chloroform and stir to dissolve, add 5ml of phosphorus trichloride to react overnight at room temperature, slowly add 100ml of ice water, 5g Sodium hydroxide solid was added twice with 50ml of chloroform for ex...

Embodiment 2

[0028] (1) Quinoxaline-2-ethyl-3-methyl-N1, N4-dioxide

[0029] Add benzofurazan (26.3g) to 2-pentanone (17g), K 2 CO 3 (50g), CHCl 3 (200ml), drip n-butylamine (28.22g) within 1h at 40℃ under stirring, continue stirring for 5h, filter out K 2 CO 3 , Vacuum distillation and concentration, add isopropanol, set ice water to precipitate out. After filtration, 40 g of yellow solid containing a small amount of benzofurazan was obtained, and 30.7 g of yellow needle-like crystals were obtained by recrystallization from ethanol several times. The reaction system will explode when the temperature exceeds 60°C.

[0030] (2) Quinoxaline-2-ethyl-3-methyl-N1-oxide

[0031] Weigh 1g of quinoxaline-2-ethyl-3-methyl-N1,N4-dioxide, add 30ml of chloroform and stir to dissolve, add 4.5g of sodium borohydride to react overnight at room temperature, slowly add 100ml of ice water, 5g Sodium hydroxide solid was added twice with 50ml of chloroform for extraction, the water layer was discarded, the organic...

Embodiment 3

[0033] (1) Quinoxaline-2-ethyl-3-methyl-N1, N4-dioxide

[0034] Add benzofurazan (26.3g) to 2-pentanone (17g), K 2 CO 3 (50g), CH 2 Cl 2 (200ml), drip n-butylamine (28.22g) in 1h at 50℃ with stirring, continue stirring for 5h, filter out K2CO3, concentrate by distillation under reduced pressure, add isopropanol, and place in ice water to precipitate precipitation. After filtration, 40.8 g of yellow solid containing a small amount of benzofurazan was obtained, and 32.9 g of yellow needle-like crystals were obtained by recrystallization from ethanol several times. The reaction system will explode when the temperature exceeds 60°C.

[0035] (2) Quinoxaline-2-ethyl-3-methyl-N1-oxide

[0036] Weigh 1g quinoxaline-2-ethyl-3-methyl-N1,N4-dioxide, add 30ml dichloromethane and stir to dissolve, add 5ml trimethyl phosphite to react overnight at room temperature, slowly add 100ml ice water, 5g of solid sodium hydroxide was added twice with 50ml of dichloromethane for extraction, the aqueous l...

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Abstract

The invention discloses a synthetic method of quinoxaline-2-ethyl-3-methyl-N1-oxide, which belongs to the technical field of biochemical industry. The molecular formula of the quinoxaline-2-ethyl-3-methyl-N1-oxide is C11H12N2O, and the quinoxaline-2-ethyl-3-methyl-N1-oxide is a quinoxaline drug metabolism product. The method comprises the following steps of: performing loop enclosing and reduction on benzofuraxan serving as a raw material to obtain a mixture of quinoxaline-2-ethyl-3-methyl-N1-oxide and N4-oxide; and performing column chromatography separation on the mixture to obtain a high-purity product. In the synthetic method, a simple and readily-available ordinary solvent is taken as a reaction medium, instruments and reaction conditions used in the method are very easy to implement, synthesis steps are simple, and an obtained product has higher purity.

Description

Technical field [0001] The invention belongs to the technical field of biochemical industry, and specifically relates to a method for synthesizing quinoxaline-2-ethyl-3-methyl-N1-oxide. Background technique [0002] Quinoxaline drugs have quinoxaline-N 1 , N 4 -A class of chemically synthesized animal-specific drugs with antibacterial and growth-promoting effects with the basic structure of dioxide, mainly including a class of new veterinary drugs with independent intellectual property rights in my country, such as quinenone and methaquine. At present, the safety of quinoxaline drugs is a hot topic of food safety concern. Veterinary drug residues in animal products can cause harm to human health and cause direct obstacles to the development of the industry. Therefore, the veterinary drug metabolism laboratory should solve an important scientific and technological problem to avoid veterinary drug residues. When studying the metabolic pathways of such drugs, it was found that such ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/52
Inventor 高海翔李松卿张素霞
Owner CHINA AGRI UNIV