Continuous preparation method for 2-aminopyrrolyl-3-ethyl carboxylate

A technology of ethyl carboxylate and aminopyrrole, which is applied in the field of continuous preparation of ethyl 2-aminopyrrole-3-carboxylate, can solve the problems of low yield of ethyl 2-aminopyrrole-3-carboxylate, etc. Achieve the effects of controllable material ratio, high yield and avoid amplification effect

Active Publication Date: 2019-12-31
ASYMCHEM LIFE SCI TIANJIN
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  • Abstract
  • Description
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Problems solved by technology

[0005] The main purpose of the present invention is to provide a continuous preparation method of ethyl 2-aminopyrrole-3-ca

Method used

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  • Continuous preparation method for 2-aminopyrrolyl-3-ethyl carboxylate

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preparation example Construction

[0029] In order to solve the problem of low yield of ethyl 2-aminopyrrole-3-carboxylate, the application provides a continuous preparation method of ethyl 2-aminopyrrole-3-carboxylate, comprising: chloral The solution is continuously fed into the first continuous reactor to carry out continuous acid-catalyzed depolymerization of chloral to obtain a chloroacetaldehyde solution; 3-amino-3-imino ethyl propionate solution, alkali solution and chloroacetaldehyde solution are continuously fed into the second continuous reactor to carry out condensation reaction to obtain ethyl 2-aminopyrrole-3-carboxylate, chloral aldehyde solution, 3-amino-3-iminopropane Ethyl acid solution and alkali solution are organic solutions.

[0030] The continuous preparation method of the present application uses structurally stable chloral as a raw material to continuously prepare commercially available and perishable anhydrous chloroacetaldehyde, and the obtained chloroacetaldehyde is dispersed in the s...

Embodiment 1

[0044] Step1: Add 50 g (0.21mol, 1eq) of chloral into the feeding bottle, then add 500 ml of chloroform, 0.32 g (2.13mmol, 1%eq) of trifluoromethanesulfonic acid, stir until dissolved, A chloral solution was obtained.

[0045] Fill a 30 ml white steel coil with chloroform, adjust the temperature to 155-165 °C (the target temperature is 160 °C), control the pressure at 0.4-0.8 MPa (the target pressure is 0.5-1.0 MPa), and after the temperature stabilizes for 10 min, It can be used for feeding.

[0046] Set the flow rate of the chloral aldehyde solution to 4.34 g / min, the chloral aldehyde solution enters the 30 ml coil tube for reaction, the retention time is 10 min, and the chloroform solution of the chloral aldehyde is obtained, and the NMR internal standard method is used to calculate Chloroacetaldehyde yield is 80%, content 4.9%.

[0047] Step2: Add 15g (0.12mol, 1eq) ethyl 3-amino-3-iminopropionate and 225 mL tetrahydrofuran into the mixing bottle, stir and dissolve to ob...

Embodiment 2

[0056] Step1: Add 50 g (0.21mol, 1eq) of chloral to the feeding bottle, then add 500 ml of ethyl acetate and 0.32 g (2.13mmol, 1%eq) of trifluoromethanesulfonic acid, and stir until Dissolved to obtain chloral aldehyde solution.

[0057] Fill a 30 ml white steel coil with ethyl acetate, adjust the temperature to 155-165°C (the target temperature is 160°C), control the pressure at 0.4-0.8 MPa (the target pressure is 0.5-1.0 MPa), and keep the temperature stable for 10 min After that, the feeding can be carried out.

[0058] The flow rate of the chloral solution is set as 2.72g / min, and the chloral solution enters a 30 ml coil tube for reaction, and the retention time is 10 min to obtain the ethyl acetate solution of chloroacetaldehyde, chloroacetaldehyde The yield is 73%, and the content is 7.2%.

[0059] Step2: Add 15g (0.12mol, 1eq) ethyl 3-amino-3-iminopropionate and 225 mL tetrahydrofuran into the mixing bottle, stir and dissolve to obtain ethyl 3-amino-3-iminopropionate ...

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Abstract

The invention provides a continuous preparation method for 2-aminopyrrolyl-3-ethyl carboxylate. The preparation method comprises the steps: continuously feeding a trichloroacetaldehyde solution to a first continuous reactor to carry out continuous acid catalyzed depolymerization on trichloroacetaldehyde, so as to a chloroacetaldehyde solution; and continuously feeding a 3-amino-3-imidoethyl propionate solution, an alkali solution and the chloroacetaldehyde solution to a second continuous reactor for a condensation reaction, thereby obtaining the 2-aminopyrrolyl-3-ethyl carboxylate. According to the continuous process, the restriction to anhydrous chloroacetaldehyde is broken through, the anhydrous chloroacetaldehyde is prepared by a continuous reaction, the reaction speed is higher than that of batches, and the yield is higher; and when the prepared chloroacetaldehyde solution is directly applied to the condensation reaction of next step, the material proportioning ratio is more controllable, the front and rear two steps can be compatible, and thus, the yield of the 2-aminopyrrolyl-3-ethyl carboxylate is globally increased. In addition, due to the continuous process, a scaling effect of the batches is avoided, and high yield during industrial application is also guaranteed.

Description

technical field [0001] The invention relates to the technical field of synthesis of ethyl 2-aminopyrrole-3-carboxylate, in particular to a continuous preparation method for ethyl 2-aminopyrrole-3-carboxylate. Background technique [0002] Ethyl 2-aminopyrrole-3-carboxylate is an important raw material for pharmaceutical synthesis, and its synthetic routes mainly include the following: [0003] The PCT international application with the international publication number WO2016 / 073891A1 discloses that chloroacetaldehyde and ethyl 3-amino-3-iminopropionate are refluxed in triethylamine and ethyl acetate for 20 min to prepare the target compound, Yield 39%. The PCT international application with the international publication number WO2017 / 004408A1 disclosed that the target compound was prepared by reflux reaction of chloroacetaldehyde and ethyl 3-amino-3-iminopropionate in ethyl acetate for 20 min, with a yield of 47% . In 2018 / Tetrahedron Letters59 (2018), it was reported tha...

Claims

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Application Information

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IPC IPC(8): C07D207/34C07C45/60C07C47/14
CPCC07C45/60C07D207/34C07C47/14
Inventor 洪浩张恩选卢江平申慰张涛符旭
Owner ASYMCHEM LIFE SCI TIANJIN
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