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Method for continuously preparing 2-benzyl isoindolinone compound by adopting microchannel reactor

A technology of benzyl isoindolinone and micro-channel reactor, which is applied in directions such as organic chemistry, fermentation, etc., can solve the problems of hidden dangers of safety and environment, high cost of industrial scale-up production, limited practicability and the like, and achieves low production cost, The effect of good product quality and short reaction time

Pending Publication Date: 2021-09-28
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the aforementioned traditional synthetic methods, noble transition metals are usually required as catalysts, and toxic carbon monoxide or flammable hydrogen are also indispensable for the transformation, which greatly limits the practicability of these methods.
These defects not only bring safety and environmental hazards, but also bring higher costs to industrial scale-up production

Method used

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  • Method for continuously preparing 2-benzyl isoindolinone compound by adopting microchannel reactor
  • Method for continuously preparing 2-benzyl isoindolinone compound by adopting microchannel reactor
  • Method for continuously preparing 2-benzyl isoindolinone compound by adopting microchannel reactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the synthesis of compound 2a

[0046] Inject 10 mL of aqueous solution of 1 mmol of ophthalmic alcohol, alcohol oxidase (700 U), flavin adenine dinucleotide (FAD, 6 μmol, 5 mg), and hydrogen peroxide reductase (0.02 μmol, 4 mg) into syringe A , air is drawn into syringe B, and the flow rate of the two samples is 56.25 μL min -1 After being pumped into the mixer, it is filled with nano MnO2 The column microreactor 1 was reacted at 40°C for 50min. Inject the acetonitrile solution of benzylamine 1a (1 mmol, 0.1 M) into syringe C and the effluent from microreactor 1 through the mixer at a flow rate of 56.25 μL min -1 Pump into coil microreactor 2 and react at 50°C for 5min. Add appropriate amount of water and ethyl acetate to the collected reaction solution for extraction, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the crude product, which can be separated by column chromatography to obtain the target product 2a with ...

Embodiment 2

[0047] Embodiment 2: the synthesis of compound 2b

[0048] Inject 10 mL of aqueous solution of 1 mmol of ophthalmic alcohol, alcohol oxidase (700 U), flavin adenine dinucleotide (FAD, 6 μmol, 5 mg), and hydrogen peroxide reductase (0.02 μmol, 4 mg) into syringe A , air is drawn into syringe B, and the flow rate of the two samples is 56.25 μL min -1 After being pumped into the mixer, it is filled with nano MnO 2 The column microreactor 1 was reacted at 40°C for 50min. Inject the acetonitrile solution of 2-methylbenzylamine 1b (1mmol, 0.1M) into syringe C and the effluent from microreactor 1 through the mixer at a flow rate of 56.25 μL min -1 Pump into coil microreactor 2 and react at 50°C for 5min. An appropriate amount of water and ethyl acetate were added to the collected reaction solution for extraction, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain a crude product, and separated by column chromatography to obtain the target product 2b...

Embodiment 3

[0049] Embodiment 3: the synthesis of compound 2c

[0050] Inject 10 mL of aqueous solution of 1 mmol of ophthalmic alcohol, alcohol oxidase (700 U), flavin adenine dinucleotide (FAD, 6 μmol, 5 mg), and hydrogen peroxide reductase (0.02 μmol, 4 mg) into syringe A , Air was sucked into syringe B, and the two samples were pumped into the mixer at a flow rate of 56.25 μL min-1 and then entered into the column microreactor 1 filled with nanometer MnO2 to react at 40°C for 50 minutes. Inject the acetonitrile solution of 4-methoxybenzylamine 1c (1mmol, 0.1M) into the syringe C and pump the effluent from the microreactor 1 into the coil microreactor 2 through the mixer at a flow rate of 56.25 μL min-1. React at 50°C for 5 minutes. Add appropriate amount of water and ethyl acetate to the collected reaction solution for extraction, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a crude product, which can be separated by column chromatography to obt...

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Abstract

The invention discloses a method for continuously preparing a 2-benzyl isoindolinone compound by adopting a microchannel reactor, which comprises the following steps: (1) respectively and simultaneously pumping a mixed solution containing 1,2-Benzenedimethanol, alcohol oxidase, flavin adenine dinucleotide and hydrogen peroxide reductase and air into a microchannel reaction device; carrying out a first reaction in a first microreactor containing nano MnO2; and (2) respectively and simultaneously pumping the first reaction effluent and a benzylamine compound solution into a second microreactor, and carrying out a second reaction to obtain the 2-benzyl isoindolinone compound as shown in a formula IV. The method has the advantages of short reaction time, high reaction conversion rate, few side reactions, small toxicity and pollution, low production cost, good product quality and the like, does not use noble metal catalysis in the reaction process, is green, environment-friendly, energy-saving and efficient, is suitable for popularization and application, and solves the problems of long reaction time, harsh reaction conditions and need of noble metal catalytic catalyst in the prior art.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for continuously preparing 2-benzylisoindolinone compounds by using a microchannel reactor. Background technique [0002] Isoindolinones are an important class of heterocyclic compounds, which are commonly found in natural products and drug molecules. Among them, isoindolin-1-ones have attracted extensive attention due to their important biological activities and are used in the pharmaceutical industry. For example: anti-inflammatory analgesic drug indoprofen (Clinical Pharmacology & Therape Utics, 1975, 17 (3).) . , antineoplastic drug lenalidomide (Blood,2005,106(13):4050-4053.), and one of the most famous representative drugs, thalidomide (Tetrahedron, 2004,60,271-274) has the structure of isoindolinone, which is used to treat leprosy (Int.Arch.Allerg.ImmUnol.1998,116,60-66.) and rheumatoid Arthritis (J.RheUmatol.1999,26,2344-347) and other diseases. ...

Claims

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Application Information

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IPC IPC(8): C12P17/10C07D209/46
CPCC12P17/10C07D209/46Y02P20/55
Inventor 郭凯王舒展杨照方正朱宁刘成扣何伟
Owner NANJING UNIV OF TECH
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