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Method of preparing furfural oxime acid

A technology of furoxamic acid and furylacetic acid, applied in the direction of organic chemistry, can solve the problems of low yield, difficult to realize reaction conditions, unsuitable for industrial production, etc., achieve high yield, reduce reaction steps, and improve efficiency

Active Publication Date: 2014-07-16
SHANDONG JIANZHU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Route (1) uses highly corrosive sulfur oxychloride and highly toxic cyanide, which is not suitable for industrialized production; route (2) and route (3) are all difficult to realize because of reaction conditions, and the yield is all low

Method used

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  • Method of preparing furfural oxime acid

Examples

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Effect test

Embodiment 1

[0042] (1) Preparation of 2-oxo-2-furylacetic acid:

[0043] Add 110g (1.0mol, M=110g / mol) 2-acetylfuran, 400mL water, and 93.5g sodium nitrite (1.5mol, M=69g / mol) into a three-necked flask equipped with a stirrer, condenser, and thermometer, and stir Dissolve and heat up to 30°C, start to add 150g of 36% hydrochloric acid (M=37.5g / mol) dropwise, with the addition of hydrochloric acid, the reaction temperature gradually rises, cool with cooling water to control the reaction temperature at 4°C, and add hydrochloric acid evenly for 3 hours In the reaction flask, the dropwise addition was completed and the heat preservation reaction was carried out for 2 hours. At this time, the pH value of the reaction solution was about 4.0. Add 4.4 g of ionic liquid 1,3-dimethylimidazolium bisulfate catalyst and react for 1 hour. Add dichloromethane and stir Extract for 0.5h, let stand to separate layers. The organic phase is distilled to recover dichloromethane, and the unreacted 2-acetylfur...

Embodiment 2

[0048] (1) Preparation of 2-oxo-2-furylacetic acid:

[0049] Add 110g (1.0mol, M=110g / mol) 2-acetylfuran, 400mL water, and 93.5g sodium nitrite (1.5mol, M=69g / mol) into a three-necked flask equipped with a stirrer, condenser, and thermometer, and stir Dissolve and heat up to 30°C, start to add 120g of 36% hydrochloric acid (1.15mol, M=37.5g / mol) dropwise, with the addition of hydrochloric acid, the reaction temperature gradually rises, the cooling water is cooled to control the reaction temperature at 4°C, and control it for 3 hours Add hydrochloric acid evenly in the reaction bottle, and keep the temperature for 2 hours after the dropwise addition. At this time, the pH value of the reaction solution is about 4.0. Add 5.5 g of ionic liquid 1-butyl-3-methylimidazole trifluoromethanesulfonate catalyst, and react 1 Hours, dichloromethane was added, stirred and extracted for 0.5h, and the layers were left to stand. The organic phase is distilled to recover dichloromethane, and th...

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Abstract

The invention relates to a method of preparing furfural oxime acid. The method comprises the steps of (1) mixing acetyl furan, sodium nitrite and hydrochloric acid to carry out oximation to generate ketoxime, carrying out Beckmann rearrangement reaction on the ketoxime in the presence of a Br phi nsted acid ionic liquid catalyst to generate amid, and carrying out hydrolysis, separation and purification on the amid under the acidic condition to obtain 2-oxo-2-furyl acetic acid; (2) carrying out silicate reaction on the 2-oxo-2-furyl acetic acid and a methoxamine salt in a solvent under the acidic condition (wherein a pH value is2.0-6.0), and carrying out separation and purification to obtain the furfural oxime acid. By virtue of adopting the method, the product yield is high, the reaction steps are less, and three-waste pollution is not generated.

Description

technical field [0001] The invention relates to a synthesis method of a pharmaceutical intermediate, in particular to a method for preparing furoxamic acid, which belongs to the technical field of chemical synthesis. Background technique [0002] Furoxamic acid, whose chemical name is ((Z)-2-(furan-2-yl)-2-methoxyiminoacetic acid), is an important pharmaceutical intermediate. It is mainly used for the production of the third-generation cephalosporin antibiotic - cefuroxime acid. In the application of preparing cefuroxime acid, it is mainly used in the form of furoxamic acid amine salt. Its traditional preparation process is mainly prepared by the oximation reaction of 2-oxo-2-furyl acetic acid and methoxyamine. At room temperature, 2-oxo-2-furyl acetic acid reacted with methoxyamine in 50% ethanol as solvent to form furoxamic acid, and the yield was only 61%. Due to the low melting point of furoxamic acid, strong acidity and poor crystal form, it is easy to absorb moistur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/54
CPCC07D307/54
Inventor 任会学孙友敏王琦魏小锋高志敏姜佳慧
Owner SHANDONG JIANZHU UNIV
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