Preparation method of mequindox

A technology of acemequine and acetylacetone, applied in the field of preparation of acemequine, can solve the problems of low product yield and purity, many steps, long reaction time and the like, and achieve the effects of improving purity, reducing loss and reducing reaction time

Active Publication Date: 2019-01-22
河北美荷药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the problems of many steps, long reaction time, and low product yield and purity in the exi

Method used

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  • Preparation method of mequindox
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  • Preparation method of mequindox

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A kind of preparation method of acetylmethaquine:

[0048] Add 920ml of methanol and 91.08g (0.66mol) of o-nitroaniline in a 500mL three-necked flask equipped with electromagnetic stirring, reflux condenser and thermometer, add 40.99g of NaOH / attapulgite compound to it, and add carboxymethyl fiber Add 18.22 g of plain sodium, stir and heat at 30°C to make it completely dissolve. Then, 68.31 g of sodium hypochlorite (containing 5% available chlorine) was slowly added dropwise, the temperature was controlled at 30° C., and the dropwise addition was completed within 3 hours. Keep warm at 30°C for 2 hours to complete the reaction.

[0049] Add 97ml (0.9372mol) of acetylacetone, stir to dissolve it, keep it warm at 35°C for 8h, place it at room temperature for 12h, wash out a lot of solids, filter, and recrystallize twice with ethanol to get yellow needle crystals, 120°C After drying for 2 hours, acemetquine was obtained with a total yield of 84.5%. The melting point is 1...

Embodiment 2

[0054] A kind of preparation method of acetylmethaquine:

[0055]Add 575ml of methanol and 91.08g (0.66mol) of o-nitroaniline in a 500mL three-necked flask equipped with electromagnetic stirring, reflux condenser and thermometer, and add 45.54g of NaOH / attapulgite compound to it, and then carboxymethyl fiber Add 22.77 g of plain sodium, stir and heat at 25°C to make it completely dissolve. Then, 72.86 g of sodium hypochlorite (containing 5% available chlorine) was slowly added dropwise, the temperature was controlled at 25° C., and the dropwise addition was completed within 3 hours. Keep warm at 25°C for 2.5 hours to complete the reaction.

[0056] Add 68ml (0.66mol) of acetylacetone, stir to dissolve it, keep it warm at 25°C for 20h, place it at room temperature for 12h, wash out a large amount of solids, filter, and recrystallize twice with ethanol to obtain yellow needle crystals, 120°C After drying for 2 hours, acemetquine was obtained with a total yield of 78.9%. The m...

Embodiment 3

[0060] A kind of preparation method of acetylmethaquine:

[0061] Add 1150ml of methanol and 91.08g (0.66mol) of o-nitroaniline in a 500mL three-necked flask equipped with electromagnetic stirring, reflux condenser and thermometer, and add 27.32g of NaOH / attapulgite compound to it, and add carboxymethyl fiber Add 13.66 g of plain sodium, stir and heat at 35°C to dissolve it completely. Then, 63.76 g of sodium hypochlorite (containing 5% available chlorine) was slowly added dropwise, the temperature was controlled at 35° C., and the dropwise addition was completed within 3 hours. Keep warm at 35°C for 2 hours to complete the reaction.

[0062] Add 116ml (1.122mol) of acetylacetone, stir to dissolve it, incubate at 40°C for 2h, place at room temperature for 12h, wash out a large amount of solids, filter, and recrystallize twice with ethanol to obtain yellow needle crystals, dry at 120°C After 2h, acemetquine was obtained with a total yield of 71.8%. The melting point is 152-1...

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Abstract

The invention provides a preparation method of mequindox. The preparation method comprises the step of performing reaction by taking ortho-nitroaniline, sodium hypochlorite and acetylacetone as raw materials, taking an NaOH/attapulgite compound as a catalyst and taking sodium carboxymethyl cellulose as a solubilizing agent and a homogenizing agent so as to obtain the mequindox. The preparation method of the mequindox, provided by the invention, realizes the purpose of one-step preparation of the mequindox, omits the intermediate treatment step of benzofurazan, and is simple in technology and high in production efficiency. The purity of the prepared mequindox product can reach 99% or more, and the total yield of the prepared mequindox product can reach 84.5% or more, which is equivalent tosingle-step yield of 90% or more, so that the prepared mequindox product has broad application prospects.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical and chemical production, in particular to a preparation method of acemethaquine. Background technique [0002] Acetylmethaquine (Shirella net), chemical name: 3-methyl-2-acetylquinoxaline-1,4-dioxide, has antibacterial and animal growth-promoting effects, and has a strong effect on Gram-negative bacteria For positive bacteria, it has a strong effect on Treponema, and is effective against piglet yellow scour, pullorum, calf diarrhea, paratyphoid fever, Pasteurella avian, chick pullorum, and chicken Escherichia coli. . [0003] The present stage about the synthetic technique of acetylmethaquine mainly is: take o-nitroaniline and acetylacetone as raw material, adopt the synthetic route of two-step method, the first step, under alkaline condition, sodium hypochlorite and o-nitroaniline carry out cyclization reaction to obtain benzofurazan, which is centrifuged, washed with water, and dried to...

Claims

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Application Information

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IPC IPC(8): C07D241/52
CPCC07D241/52
Inventor 孟凡桥梁剑平梁妍陈虹王闪孟建王卫华
Owner 河北美荷药业有限公司
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