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Method for synthesizing pyridine compound by using microchannel reaction device

A microchannel reaction and ester compound technology, which is applied in chemical instruments and methods, chemical/physical processes, chemical/physical/physical chemical processes, etc., can solve the problems of low reaction efficiency, long reaction time, and complicated reaction steps. Achieve the effect of speeding up the reaction rate, green reaction conditions, and easy reaction process

Active Publication Date: 2021-08-27
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Purpose of the invention: the present invention is aimed at the deficiencies in the prior art, and provides a method for utilizing a microchannel reaction device to synthesize pyridine derivatives, so as to solve the reaction problems in the prior art The steps are cumbersome, the reaction time is long, and the reaction efficiency is low. In the case of no metal catalyst, the synthesis of pyridine-containing derivatives is simple and efficient.

Method used

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  • Method for synthesizing pyridine compound by using microchannel reaction device
  • Method for synthesizing pyridine compound by using microchannel reaction device
  • Method for synthesizing pyridine compound by using microchannel reaction device

Examples

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Effect test

Embodiment 1

[0048] Dissolve 1mmol (0.261g) of (2E,4E)-4-(acetoxyimino)-4-phenylbut-2-enoic acid ethyl ester, 0.1mmol (0.0125g) of ferrous chloride in 10mL In 1,2-dichloroethane, the resulting mixed solution is recorded as solution A; 2mmol (0.322g) of N-(1-phenylvinyl)acetamide was dissolved in 10mL of 1,2-dichloroethane , the resulting mixed solution is recorded as solution B, and then solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, the flow rate is 0.5mL / min, and they enter the microchannel reaction after being mixed by a Y-type mixer. React at 120° C. for 8 minutes in a microreactor (the inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5 mm, and the volume of the polytetrafluoroethylene tube is 4 mL). The organic phase was obtained from the discharge of the microreactor, and concentrated in vacuo to obtain the crude product, which was separated by developer column chromatography with a rati...

Embodiment 2

[0050] 1mmol (0.275g) of (2E,4E)-4-(acetoxyimino)-4-(p-tolyl)but-2-enoic acid ethyl ester, 0.1mmol (0.0125g) of ferrous chloride Dissolve in 10mL of 1,2-dichloroethane, and the resulting mixed solution is recorded as solution A; 2mmol (0.322g) of N-(1-phenylvinyl)acetamide is dissolved in 10mL of In ethyl chloride, the resulting mixed solution is recorded as solution B, and then solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, and the flow rate is 0.5mL / min respectively. React at 120° C. for 8 minutes in a microchannel reactor (the inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5 mm, and the volume of the polytetrafluoroethylene tube is 4 mL). The organic phase was obtained from the discharge of the microreactor, concentrated in vacuo to obtain the crude product, and separated by column chromatography with a developing agent with a ratio of petroleum ether to ethyl acetate of 5:1 ...

Embodiment 3

[0052] Add 1mmol (0.295g) of (2E,4E)-4-(acetoxyimino)-4-(p-chlorophenyl)but-2-enoic acid ethyl ester, 0.1mmol (0.0125g) of ethylene chloride Iron was dissolved in 10mL of 1,2-dichloroethane, and the resulting mixed solution was recorded as solution A; 2mmol (0.322g) of N-(1-phenylvinyl)acetamide was dissolved in 10mL of 1,2- In dichloroethane, the resulting mixed solution is recorded as solution B, and then solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, and the flow rate is 0.5mL / min respectively, after being mixed by a Y-type mixer Enter the microchannel reactor (the inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5mm, and the volume of the polytetrafluoroethylene tube is 4mL) and react at 120°C for 8min. The organic phase was obtained from the discharge of the microreactor, concentrated in vacuo to obtain the crude product, and separated by column chromatography with a developi...

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Abstract

The invention discloses a method for synthesizing a pyridine compound shown as III by using a micro-channel reaction device, which comprises the following steps: taking an alpha, beta-unsaturated ketoxime ester compound I and an N-acetyl amide compound II as reaction raw materials, adding a catalyst, and continuously reacting by using the micro-channel reaction device to prepare the pyridine compound. Compared with the prior art, the novel pyridine compound is prepared by taking the alpha, beta-unsaturated ketoxime ester compound and the N-acetyl amide compound as substrates, multi-component reaction is avoided, and the product is rapidly and efficiently synthesized by using the metal catalyst. Wherein R1 and R2 are independently selected from non-substituted or substituted phenyl, furyl, naphthyl or C1-C5 alkyl; and the substituted phenyl group is selected from phenyl groups substituted by halogen, C1-C5 alkyl groups or C1-C5 alkoxy groups.

Description

technical field [0001] The invention belongs to the technical field of preparation of pyridine compounds, in particular to a method for synthesizing pyridine compounds using a microchannel reaction device. Background technique [0002] Substituted pyridine compounds are unique scaffolds in medicinal chemistry and are versatile building blocks for constructing natural products, functional materials, agrochemicals and pharmaceuticals, therefore, efforts are being made to develop new transformation methods to construct various pyridine derivatives . In synthetic chemistry, the synthesis of various pyridine compounds using oxime derivatives has attracted widespread attention of chemists. [0003] At present, the preparation methods of pyridine derivatives mainly include: (1) oxime esters and electron-deficient olefins generate pyridine derivatives through [3+3] cyclization reaction under the condition of copper catalysis, which can be found in literature (Angew.Chem. , Int.Ed....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/79C07D405/04B01J19/00
CPCC07D213/79C07D405/04B01J19/0093
Inventor 郭凯徐高晨段金电延欢张赛邬庆环季栋沈磊李玉光
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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