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Synthesis method of quinocetone

A synthetic method and quinocetone technology, which is applied in the field of synthesis of veterinary drug quinocetone, can solve the problems of difficulty in obtaining high-yield qualified products and difficulties in purification, and achieve the effects of simple and convenient production process, excellent yield, and mild reaction conditions

Pending Publication Date: 2019-07-12
SUZHOU HUADAO BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Due to the particularity of the quinoxaline structure and the instability of α, β-unsaturated carbonyl compounds, the color of the produced quinocetone is usually darker, and even more off-brick red; and impurities are often generated, such as the following 2 impurities It is often formed in the reaction and is difficult to remove; this makes purification difficult, making it difficult to obtain qualified products with high yield and high purity

Method used

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  • Synthesis method of quinocetone
  • Synthesis method of quinocetone
  • Synthesis method of quinocetone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Weigh 1.2 g of valine, 1 g of 4-picoline, and 5 g of diethylene glycol, add them into a 250 ml reaction flask, add 80 ml of purified water, and stir to clarify the system.

[0033] Weighed 21.8 g of methaquine and 13.8 g of benzaldehyde respectively, added them to the above catalytic system, heated to 40° C. for 6 hours, and HPLC detected that the reaction of methaquine was complete, cooled, and suction filtered to obtain the crude quinocetone.

[0034] Add 60 ml of methanol to the crude quinocetone, stir for 1 hour, filter with suction, and dry in vacuum to obtain 27.6 g of the product with a yield of 90% and a purity of 98.2%.

Embodiment 2

[0036] Weigh 1 g of phenylalanine, 0.5 g of pyridine, and 2 g of triethylene glycol, add them into a 250 ml reaction flask, add 80 ml of pure water, and stir to clarify the system.

[0037] Weighed 21.8 g of methaquine and 12.8 g of benzaldehyde respectively, added them to the above catalytic system, heated to 40° C. and reacted for 4 hours, HPLC detected that the reaction of methaquine was complete, cooled, and suction filtered to obtain the crude quinocetone.

[0038] Add 80 ml of methanol to the crude quinocetone, stir for 1 hour, filter with suction, and dry in vacuum to obtain 28.1 g of the product with a yield of 92% and a purity of 98.1%.

Embodiment 3

[0040] Weigh 1.5 g of proline, 1.5 g of sodium carbonate, and 2 g of polyethylene glycol 400, add them into a 250 ml reaction flask, add 80 ml of purified water, and stir to clarify the system.

[0041] Weighed 21.8 g of methaquine and 11.8 g of benzaldehyde respectively, added them to the above catalytic system, heated to 25° C. for 5 hours, HPLC detected that the methaquine was completely reacted, cooled, and suction filtered to obtain the crude quinocetone.

[0042] Add 80 ml of methanol to the crude quinocetone, stir for 1 hour, filter with suction, and dry in vacuo to obtain 28.6 g of the product with a yield of 93% and a purity of 99.2%.

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Abstract

The invention discloses a new synthesis method of quinocetone. Quinocetone is synthesized from mequindox and benzaldehyde as raw materials by reaction in an amino acids-alkali composite catalytic system. The product yield is 90% or higher and purity can reach 99%. Besides, the catalytic system promotes rapid reaction of mequindox and benzaldehyde at a lower temperature in the water phase to prepare the high-quality product, reaction conditions are mild, yield is excellent, and the production process is simple and convenient, safe and reliable; after the product is removed, the catalytic systemcan be recycled 3 times without changing the catalytic effect, and accordingly, the production cost can be reduced.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing veterinary drug quinocetone. Background technique [0002] Quinocetone (Quinocetone) is a kind of veterinary drug developed by Lanzhou Institute of Animal Husbandry and Veterinary Medicine, Chinese Academy of Agricultural Sciences. Especially for young livestock and poultry, it has a very significant effect of antibacterial, antidiarrheal and growth promoting; it can also be used in aquaculture for antibacterial and growth promotion, improving survival rate, and can clarify water body and improve water quality. [0003] The chemical name of quinocetone is 3-methyl-2-styryl-quinoxaline-1,4-dioxide, the molecular formula is C18H14N203, the molecular weight is 306.5, and the melting point (m.P.) is 182.5-189 Appearance is light yellow or yellow-green powder, odorless, tasteless, soluble in chloroform, dimethyl sulfoxide, dioxane, slightly solub...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/52
CPCC07D241/52
Inventor 陆军刘辉吴志民刘明荣
Owner SUZHOU HUADAO BIOLOGICAL PHARMA
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