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Continuous hydrogenation method of 2-nitropyridine derivative and application thereof

A technology for nitropyridine and derivatives, which is applied in the field of continuous hydrogenation of 2-nitropyridine derivatives (II), can solve the problems of long hydrogenation reaction time, high operation requirements, and difficulty in controlling spontaneous combustion of catalysts, so as to reduce impurities The risk of generation, the effect of increasing the reaction efficiency, reducing the risk of spontaneous combustion

Active Publication Date: 2022-07-29
NANJING VCARE PHARMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The main purpose of the present invention is to provide a continuous hydrogenation method of 2-nitropyridine derivatives (II) and its application, to solve the existing problems of hydrogenation and reaction in the catalytic hydrogenation process of 2-nitropyridine derivatives. The safety requirements of the device are relatively high, the operation of the autoclave requires a large amount of labor and high operation requirements, the catalyst needs to be filtered, it is difficult to control the spontaneous combustion of the catalyst, the hydrogenation reaction time is long, the conversion rate is low, and azo impurities A and B are easily formed.

Method used

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  • Continuous hydrogenation method of 2-nitropyridine derivative and application thereof
  • Continuous hydrogenation method of 2-nitropyridine derivative and application thereof
  • Continuous hydrogenation method of 2-nitropyridine derivative and application thereof

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Experimental program
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Effect test

Embodiment 1

[0044]

[0045] The reaction column was packed with 5% Pt / C spherical catalyst, wherein the catalyst packing mass was 2.5 g, the packing height was 31 mm, the packing diameter was 4.6 mm, and the catalyst particle size was 0.5 mm, which was used as the fixed bed reactor 40.

[0046] Dissolve the raw material II-1 in methanol, prepare a solution with a mass concentration of 10%, and place it in the raw material storage tank 10; ℃, mixed with hydrogen in the T-type mixer 30 to obtain a gas-liquid mixture, and the gas-liquid ratio of the gas-liquid mixture is 50:1; the above-mentioned gas-liquid mixture is transported to the fixed-bed reactor 40 for catalytic hydrogenation. Product 1-1. Among them, the reaction temperature was 30-40 °C, the reaction pressure was 1.0 MPa, and the volumetric space velocity was 6 h -1 , run for 48 h. After being separated by the gas-liquid separation device 50, the conversion rate of the raw material is 99.6%, the product purity is 99.2%, and t...

Embodiment 2

[0049]

[0050] The reaction column was packed with 5% Pt / C spherical catalyst, wherein the catalyst packing mass was 2.5 g, the packing height was 31 mm, the packing diameter was 4.6 mm, and the catalyst particle size was 0.5 mm, which was used as the fixed bed reactor 40.

[0051] Dissolve the raw material II-2 in ethanol, prepare a solution with a mass concentration of 10%, and place it in the raw material storage tank 10; ℃, mixed with hydrogen in the T-type mixer 30 to obtain a gas-liquid mixture, and the gas-liquid ratio of the gas-liquid mixture is 40:1; the above-mentioned gas-liquid mixture is transported to the fixed-bed reactor 40 for catalytic hydrogenation. Product 1-2. Among them, the reaction temperature was 40-50 °C, the reaction pressure was 2.0 MPa, and the volumetric space velocity was 6 h -1 , run for 48 h. After being separated by the gas-liquid separation device 50, the conversion rate of the raw material is 99.6%, and the product purity is 99.1%. T...

Embodiment 3

[0053]

[0054] The reaction column was packed with 5% Pt / C spherical catalyst, wherein the catalyst packing mass was 2.5 g, the packing height was 31 mm, the packing diameter was 4.6 mm, and the catalyst particle size was 0.5 mm, which was used as the fixed bed reactor 40.

[0055] The raw material II-3 was dissolved in ethyl acetate, prepared into a solution with a mass concentration of 8%, and placed in the raw material storage tank 10; the raw material solution was preheated to 40 through the plunger pump P01, the check valve V01 and the heat exchanger H01 ~50 ℃, mix with hydrogen in the T-type mixer 30 to obtain a gas-liquid mixture, and the gas-liquid ratio of the gas-liquid mixture is 30:1; the above-mentioned gas-liquid mixture is transported to the fixed-bed reactor 40 for catalytic hydrogenation reaction , the product I-3 was obtained. Among them, the reaction temperature was 40-50 °C, the reaction pressure was 3.0 MPa, and the volumetric space velocity was 6 h -...

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Abstract

The invention provides a continuous hydrogenation method of a 2-nitropyridine derivative, which comprises the following steps: dissolving a 2-nitropyridine derivative (II) in a solvent, and mixing with hydrogen to form a gas-liquid mixture as a reaction raw material; and continuously inputting the reaction raw materials into a fixed bed reactor for catalytic hydrogenation reaction, and continuously discharging the 2-aminopyridine derivative (I). According to the method, the reaction state in the reactor can be effectively controlled, the reaction efficiency can be greatly improved, the risk of impurity generation is reduced, and the yield, the purity and the product performance stability of a target product are improved. The catalyst does not need to be filtered after the catalytic hydrogenation reaction, so that the spontaneous combustion risk of the catalyst is reduced, the catalyst has no deactivation phenomenon, and the recovered catalyst can be recycled. The method has the advantages of low cost, high yield of the 2-aminopyridine derivative (I), high purity and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a continuous hydrogenation method of 2-nitropyridine derivative (II) and application thereof. Background technique [0002] 2-Aminopyridine derivatives (I) are a class of important intermediates that are widely used in the field of biomedicine, such as the cyclin-dependent cyclin-dependent treatment of myelosuppression and small cell lung cancer approved by the US FDA on February 12, 2021. Kinase 4 / 6 (CDK4 / 6) inhibitor Trilaciclib; cyclin-dependent kinase 4 / 6 (CDK4 / 6) for metastatic breast cancer approved by the U.S. FDA on January 3, 2015 ) inhibitor Palbociclib; Dalpiciclib, a class 1 innovative drug developed by Jiangsu Hengrui Pharmaceutical Co., Ltd., approved by the State Drug Administration through the priority review and approval process in December 2021 Western medicine is used for hormone receptor-positive, human epidermal growth factor receptor 2-negative ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74C07D401/04C07D213/73C07D213/75A61P35/00
CPCC07D213/74C07D401/04C07D213/73C07D213/75A61P35/00
Inventor 郝昆明骆玉成秦小飞周西朋杨尚彦龚彦春刘永强
Owner NANJING VCARE PHARMATECH CO LTD
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