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Method for preparing 2-amino-3-methyl nitrobenzoate

A technology of methyl nitrobenzoate and methyl anthranilate, which is applied in the field of organic chemical synthesis, can solve the problems of long reaction time, cumbersome operation, and large potential safety hazard, achieve high value, improve production efficiency, and increase yield. rate effect

Active Publication Date: 2020-06-09
浙江聚贤医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The method for preparing 2-amino-3-nitrobenzoic acid methyl ester reported in the literature, or the reaction time is long, or the operation is complicated, or the safety hazard is great

Method used

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  • Method for preparing 2-amino-3-methyl nitrobenzoate
  • Method for preparing 2-amino-3-methyl nitrobenzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] (1) Phthalimide, water, sodium hydroxide and methanol are prepared in a mass ratio of 1:1.05:0.15:0.9 to prepare a phthalimide solution. The phthalimide solution and the sodium hypochlorite solution are pumped into the microchannel reactor through the metering pump at flow rates of 26.84ml / min and 32.81ml / min respectively, the reaction temperature is -5°C, and the retention time of the reaction solution is 20s. The microreactor is connected in series with the pipeline reaction; at the same time, the water is preheated, the water pump is turned on, and the flow rate is 32.81ml / min. The retention time is 300s, and the reaction solution flows out, and the methyl anthranilate solution is obtained by continuous centrifugation in the ring gap type for future use. The purity determined by liquid chromatography is greater than 97.8%, and the yield is not less than 95.0%.

[0056] (2) The methyl anthranilate solution obtained in step 1 was diluted with glacial acetic acid to ob...

Embodiment 2

[0060] (1) Phthalimide, water, sodium hydroxide and methanol are formulated into a phthalimide solution in a mass ratio of 1:1.55:0.25:1.125. The phthalimide solution and the sodium hypochlorite solution are pumped into the microchannel reactor through the metering pump at flow rates of 15.50ml / min and 24.03ml / min respectively, the reaction temperature is 5°C, and the retention time of the reaction solution is 30s. The reactor is connected in series with the pipeline reaction; at the same time, the water is preheated, the water pump is turned on, and the flow rate is 24.03ml / min. After 180 s, the reaction liquid flows out, and the methyl anthranilate solution is obtained by continuous centrifugation in annulus for future use. Different batches of effluents were sampled, and the purity determined by liquid chromatography was greater than 98.2%, and the yield was not less than 94.6%.

[0061] (2) The methyl anthranilate solution obtained in step 1 was diluted with glacial aceti...

Embodiment 3

[0065] (1) Phthalimide, water, sodium hydroxide and methanol are prepared in a mass ratio of 1:2.05:0.35:1.35 to prepare a phthalimide solution. The phthalimide solution and the sodium hypochlorite solution are pumped into the microchannel reactor through the metering pump at the flow rate of 10.50ml / min and 18.90ml / min respectively, the reaction temperature is 15°C, and the retention time of the reaction solution is 40s. The reactor is connected in series with the pipeline reaction; at the same time, the water is preheated, the water pump is turned on, and the flow rate is 18.90ml / min. After 200 s, the reaction solution flows out, and the methyl anthranilate solution is obtained by continuous centrifugation in the ring gap type for subsequent use. Different batches of effluents were sampled, and the purity determined by liquid chromatography was greater than 99.4%, and the yield was not less than 95.6%.

[0066] (2) The methyl anthranilate solution obtained in step 1 was dil...

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Abstract

The invention discloses a method for preparing methyl 2-amino-3-nitrobenzoate, which comprises the following steps: pumping a phthalimide solution and a sodium hypochlorite solution into a micro-reaction mixer, reacting, reacting with water in a tubular reactor to obtain methyl anthranilate, and continuously separating to obtain a crude product; pumping the methyl anthranilate crude product, an acetic anhydride solution and fuming nitric acid into a micro-channel reactor, mixing, reacting to obtain N-methyl nitrobenzoate, and continuously separating to obtain a crude product; pumping an N-methyl nitrobenzoate solution, concentrated sulfuric acid and water into a micro-channel reactor, mixing, and reacting to obtain a 2-amino-3-methyl nitrobenzoate crude product; recrystallizing the crude product in methanol to obtain a product, namely methyl 2-amino-3-nitrobenzoate; and the method is high in yield, good in safety and suitable for industrial production.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a method for preparing methyl 2-amino-3-nitrobenzoate. Background technique [0002] Methyl 2-amino-3-nitrobenzoate is an important organic synthesis intermediate and an important intermediate for the synthesis of benzimidazole drugs candesartan, azilsartan and ABT-472 PAPR inhibitors. It has a wide range of Value. [0003] At present, the method for synthesizing 2-amino-3-nitrobenzoic acid methyl ester mainly contains following two kinds: 1, take 3-nitrophthalic acid as raw material to obtain through monoesterification, acyl chloride, Curtius rearrangement; 2 , 2-amino-3-nitrobenzoic esterification to obtain the product. Patent CN201410181414A released a method for preparing 2-amino-3-nitrobenzoic acid methyl ester in a reactor, using 3-nitrophthalic acid and methanol as raw materials to synthesize monoesters under the catalysis of concentrated sulfuric acid, monoeste...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/56C07C227/04C07C227/42B01J19/00
CPCC07C227/04C07C227/42C07C241/00C07C227/22B01J19/0093C07C229/56C07C243/02
Inventor 王源肖燕张恩乾王俊峰周英雷汪海斌夏春年
Owner 浙江聚贤医药科技有限公司
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