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Synthesis process of beta-cyclopropylamino acrylate

A technology of cyclopropylamino acrylate and cyclopropylamino acrylic acid, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of high cost, the production of quinolone antibacterial drugs is not widely used, and achieves operation Convenience, reduced emissions, simple response effects

Inactive Publication Date: 2007-08-22
HANGZHOU NORMAL UNIVERSITY +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In this method, propiolic acid (ester) is generally all obtained by oxidation of propynyl alcohol and then esterified. Not only the cost is high but also heavy metal chromium is used to cause a large amount of oxidized waste. Therefore, the above method has not been widely used in the production of quinolone antibacterial drugs so far.

Method used

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  • Synthesis process of beta-cyclopropylamino acrylate
  • Synthesis process of beta-cyclopropylamino acrylate
  • Synthesis process of beta-cyclopropylamino acrylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Press 2.30g of metallic sodium into sodium wire and place it in a reaction bottle, add 50ml of anhydrous ether, control the temperature of the reaction solution at about 25°C, and drop the mixture of 11.8g of ethyl formate and 8.2g of methyl acetate from a constant pressure Slowly add it dropwise in the reaction bottle in the funnel, let it stand for the reaction, the reaction speed is slow at the beginning, when the reaction starts to accelerate after a period of time, a large amount of bubbles are released at the same time, when the metal sodium completely disappears, the reaction ends, and 11.6g formylacetic acid is obtained by filtration Methyl ester sodium salt, yield 93.5%.

Embodiment 2

[0043] Press 2.30g of metallic sodium into sodium wire and place it in a reaction flask, add 45ml of isopropyl ether, mix 11.8g of ethyl formate and 9.7g of ethyl acetate, and slowly drop them into the reaction flask from a constant pressure dropping funnel. In the bottle, control the temperature of the reaction solution at about 30°C. The reaction speed is slow at the beginning. After a period of time, the reaction starts to accelerate, and a large number of bubbles are released at the same time. When the metal sodium completely disappears, the reaction is over, and the sodium formyl acetate is obtained by filtration. Salt 12.7g, yield 92.0%.

Embodiment 3

[0045]Put 15.5g of cyclopropylamine sulfate into a reaction bottle containing 30ml of petroleum ether (60-90°C) (product of Hangzhou Shengli Chemical Co., Ltd.), heat up and stir to reflux, and then add 13.8g of ethyl formyl acetate sodium salt Slowly add the suspension mixed with 50ml of petroleum ether (60-90°C) into the reaction solution dropwise, the dropwise addition is completed in about 1.5 hours, and the reaction is completed after 4.5 hours of reaction, stop the reaction, cool, filter out the solid salt, and the mother liquor is under normal pressure Low boilers and most of the solvents were distilled off, and then distilled under reduced pressure to collect 14.2 g of 64-68°C / 12Pa fraction, namely ethyl β-cyclopropylaminoacrylate, with a yield of 91.6%.

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Abstract

The present invention provides synthesis process of beta-cyclopropylamino acrylate. The synthesis process includes the following steps: 1. the condensation reaction of formate and acetate in the presence of alkali metal or alkali metal hydride to produce alkali metal salt as shown; and 2. amine substituting and eliminating reaction of the alkali metal salt and ammonium salt in organic solvent to obtain beta-cyclopropylamino acrylate as shown. The present invention has simple synthesis process, convenient operation, facile material, low cost and less pollution.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing β-cyclopropylaminoacrylic acid (ester). (2) Background technology [0002] β-cyclopropylaminoacrylic acid (ester) is a key intermediate for the synthesis of quinolone antibacterial drugs such as gatifloxacin, ciprofloxacin and sparfloxacin. [0003] Quinolones have a wide antibacterial spectrum, strong antibacterial activity, and good clinical effect, and have become the most important antibacterial drugs. According to existing reports, the most economical and environmentally friendly method for synthesizing quinolone main ring compounds is to couple the key intermediate β-cyclopropylamino acrylic acid (ester) with o-halogen aroyl chloride, and then obtain it through ring closure. [0004] And the method for bibliographical report synthetic β-cyclopropylamino acrylic acid (ester) is to carry out addition reaction to make by propiolic acid (ester) and cyclopropylamine at present, and reaction formu...

Claims

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Application Information

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IPC IPC(8): C07C227/16C07C229/30
Inventor 章鹏飞顾海宁张习坤汪劲松李小玲
Owner HANGZHOU NORMAL UNIVERSITY
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