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Method for synthesizing 4-methoxy-2-nitroaniline by adopting continuous flow reactor

A technology for methoxyaniline and nitroaniline, applied in the field of organic synthesis, can solve the problems of reduced yield, side reactions, uneven heat exchange, etc., and achieves improved yield and purity, improved yield and purity, and improved reaction safety effect

Pending Publication Date: 2020-09-25
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] 2. In the reaction in the static reactor, the heat cannot be taken away in time, the heat exchange is uneven, it is easy to cause side reactions such as multi-nitration and sulfonation, and it is easy to cause fire and explosion accidents;
[0006] 3. The nature of the by-product is close to that of the product, and the post-treatment purification of the product is difficult, resulting in a decrease in yield

Method used

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  • Method for synthesizing 4-methoxy-2-nitroaniline by adopting continuous flow reactor
  • Method for synthesizing 4-methoxy-2-nitroaniline by adopting continuous flow reactor
  • Method for synthesizing 4-methoxy-2-nitroaniline by adopting continuous flow reactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] A method for the synthesis of 4-methoxy-2-nitroaniline using a continuous flow reactor, such as figure 1 Shown, synthetic route is:

[0040]

[0041] Include the following steps:

[0042] (1) Raw material preparation: Pour 96mL of glacial acetic acid and 40g of 4-methoxyaniline, 0.32mol into beaker A and stir until dissolved, weigh 64g of acetic anhydride, pour 0.63mol into beaker B, and mix in beaker C Acid (mass ratio of concentrated sulfuric acid to concentrated nitric acid is 1:1.15) 85g, 0.47mol; prepare 162.6g of 40% NaOH aqueous solution in beaker D, 1.63mol;

[0043] (2) Acetylation reaction: connect beaker A to metering pump Ⅰ, beaker B to metering pump Ⅱ, start metering pump Ⅰ and metering pump Ⅱ at the same time, pour the two solutions into continuous flow reactor Ⅰ, and react at 25°C for 133min , to obtain the reaction solution I containing 4-methoxyacetanilide; wherein, the flow rate of the metering pump I is 5mL / min, and the flow rate of the metering ...

Embodiment 2

[0048] A method for the synthesis of 4-methoxy-2-nitroaniline using a continuous flow reactor, such as figure 1 Shown, synthetic route is:

[0049]

[0050] Include the following steps:

[0051] (1) Raw material preparation: Pour 96mL of glacial acetic acid and 40g of 4-methoxyaniline, 0.32mol into beaker A and stir until dissolved, weigh 64g of acetic anhydride, pour 0.63mol into beaker B, and mix in beaker C Acid (mass ratio of concentrated sulfuric acid to concentrated nitric acid is 1:1.15) 85g, 0.47mol; prepare 162.6g of 40% NaOH aqueous solution in beaker D, 1.63mol;

[0052] (2) Acetylation reaction: connect beaker A to metering pump Ⅰ, beaker B to metering pump Ⅱ, start metering pump Ⅰ and metering pump Ⅱ at the same time, pour the two solutions into continuous flow reactor Ⅰ, and react at 25°C for 133min , to obtain the reaction solution I containing 4-methoxyacetanilide; wherein, the flow rate of the metering pump I is 5mL / min, and the flow rate of the metering ...

Embodiment 3

[0057] A method for the synthesis of 4-methoxy-2-nitroaniline using a continuous flow reactor, such as figure 1 Shown, synthetic route is:

[0058]

[0059] Include the following steps:

[0060] (1) Raw material preparation: Pour 96mL of glacial acetic acid and 40g of 4-methoxyaniline, 0.32mol into beaker A and stir until dissolved, weigh 64g of acetic anhydride, pour 0.63mol into beaker B, and mix in beaker C Acid (mass ratio of concentrated sulfuric acid to concentrated nitric acid is 1:1.15) 85g, 0.47mol; prepare 162.6g of 40% NaOH aqueous solution in beaker D, 1.63mol;

[0061] (2) Acetylation reaction: connect beaker A to metering pump Ⅰ, beaker B to metering pump Ⅱ, start metering pump Ⅰ and metering pump Ⅱ at the same time, pour the two solutions into continuous flow reactor Ⅰ, and react at 25°C for 13.3 min, to obtain the reaction solution I containing 4-methoxyacetanilide; wherein, the flow rate of the metering pump I is 50mL / min, and the flow rate of the meterin...

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Abstract

The invention relates to the technical field of organic synthesis, and discloses a method for synthesizing 4-methoxy-2-nitroaniline by using a continuous flow reactor. The method comprises the following steps: S1, respectively adding a 4-methoxyaniline solution and acetic anhydride into a continuous flow reactor I, and carrying out an acetylation reaction to obtain a reaction solution I containing4-methoxyacetanilide; S2, respectively adding a nitration reagent and the reaction solution I into a continuous flow reactor II, and carrying out a nitration reaction to obtain a reaction solution IIcontaining 4-methoxy-2-nitroacetanilide; S3, respectively adding hydrolysate and the reaction solution II into a continuous flow reactor III, and carrying out a hydrolysis reaction to obtain a reaction solution III containing 4-methoxy-2-nitroaniline; and S4, carrying out post-treatment on the reaction solution III to obtain 4-methoxy-2-nitroaniline. The method is high in reaction speed, small inamount of byproduct 4-methoxy-3-nitroaniline, high in heat and mass transfer efficiency, high in reaction safety, high in selectivity, high in yield and purity and convenient in after-treatment.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 4-methoxy-2-nitroaniline using a continuous flow reactor. Background technique [0002] Omeprazole, namely 5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)-methyl]-sulfoxide}-1H-benzimidazole , is the world's first marketed proton pump inhibitor, which has a lasting inhibitory effect on gastrin, as well as gastric acid secretion caused by acetylcholine, histamine, food or vagus nerve stimulation, and is mainly used in ulcers and esophageal acid reflux disease , gastrinoma and Helicobacter pylori infection treatment. [0003] 4-methoxy-2-nitroaniline is an important intermediate in the synthesis of omeprazole. At present, its production method mainly adopts the batch reactor process, that is, 4-methoxyaniline is used as a raw material, and is obtained through three-step reactions of acetylation, nitration and hydrolysis, and the nitration reac...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C231/12C07C233/25C07C213/02C07C217/84B01J19/24
CPCC07C231/02C07C231/12C07C213/02B01J19/245C07C233/25C07C217/84Y02P20/55
Inventor 郭安勇刘志伟王银何紫权周家焱郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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