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Method for preparing medical intermediate pyranoquinoline derivative

A technology of pyranoquinoline and furoquinoline, which is applied in the field of organic synthesis, can solve the problems of easily polluted environment, catalyst catalytic efficiency and low utilization rate of reaction raw materials, catalyst and reaction solvent cannot be recycled and the like, and achieves economical and High environmental benefits, high efficiency and selectivity, and the effect of suppressing the production of by-products

Active Publication Date: 2020-08-25
深圳尚诺生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to overcome the shortcomings of existing pharmaceutical intermediate pyranoquinoline derivative preparation methods, such as relatively low catalytic efficiency of catalysts and relatively low utilization rate of reaction raw materials, non-recyclable use of catalysts and reaction solvents, and easy pollution of the environment. A method for preparing pharmaceutical intermediate pyranoquinoline derivatives is provided

Method used

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  • Method for preparing medical intermediate pyranoquinoline derivative
  • Method for preparing medical intermediate pyranoquinoline derivative
  • Method for preparing medical intermediate pyranoquinoline derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 1.0mmol benzaldehyde and 1.0mmol propanediol to a 50ml single-necked bottle with a spherical condenser and a stirring bar containing 5ml of mixed solvent (the volume ratio of methanol-dimethylacetamide-water is 2:1:1). Nitrile, 1.0 mmol 4-hydroxyquinolin-2-one, stirred at room temperature, mixed evenly, and then added 0.09 g of magnetic nanomaterial catalyst. Heat in an oil bath, evenly heat up to solvent reflux (solvent vapor does not exceed the second ball of the spherical condenser), keep reflux for 91min, TLC (thin plate chromatography) detection, the raw material point disappears, and the reaction is over. Turn off the heating and stirring, immediately use a magnet to absorb the magnetic nanomaterial catalyst, transfer the remaining reaction solution to a beaker and gradually cool to room temperature, at this time a large amount of solids are precipitated, crush the solids, let stand for 8 hours, filter with suction, and filter residue after 95 After washing wi...

Embodiment 2

[0031] Add 1.0mmol o-chlorobenzaldehyde, 1.2mmol Malononitrile and 1.0 mmol 4-hydroxyquinolin-2-one were stirred at room temperature and mixed uniformly, and then 0.10 g of magnetic nanomaterial catalyst was added. Heat in an oil bath, evenly heat up to solvent reflux (solvent vapor does not exceed the second ball of the spherical condenser), keep reflux for 94min, TLC (thin plate chromatography) detection, the raw material point disappears, and the reaction is over. Turn off the heating and stirring, immediately use a magnet to absorb the magnetic nanomaterial catalyst, transfer the remaining reaction solution to a beaker and gradually cool to room temperature, at this time a large amount of solids are precipitated, crush the solids, let stand for 8 hours, filter with suction, and filter residue after 95 After washing with % ethanol aqueous solution (4ml×3) and vacuum drying at 85°C for 12h, 0.32g of the product was obtained. The purity was 98.7% as determined by high perform...

Embodiment 3

[0036] Add 1.0mmol p-chlorobenzaldehyde, 1.1mmol Malononitrile and 1.0 mmol 4-hydroxyquinolin-2-one were stirred at room temperature and mixed evenly, and then 0.08 g of magnetic nanomaterial catalyst was added. Heat in an oil bath, evenly heat up to solvent reflux (solvent vapor does not exceed the second ball of the spherical condenser), keep reflux for 87min, TLC (thin plate chromatography) detection, the raw material point disappears, and the reaction is over. Turn off the heating and stirring, immediately use a magnet to absorb the magnetic nanomaterial catalyst, transfer the remaining reaction solution to a beaker and gradually cool to room temperature, at this time a large amount of solids are precipitated, crush the solids, let stand for 8 hours, filter with suction, and filter residue after 95 After washing with % ethanol aqueous solution (4ml×3) and vacuum drying at 85°C for 12h, 0.32g of the product was obtained. The purity was 99.1% as determined by high performanc...

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Abstract

The invention discloses a method for preparing a medical intermediate pyranoquinoline derivative, and belongs to the technical field of organic synthesis. According to the method for preparing a medical intermediate pyranoquinoline derivative, reaction raw materials including aromatic aldehyde, an active methylene compound, 4-hydroxyquinoline-2-one and a catalyst are respectively added into a reaction solvent and uniformly mixed, and heating reflux reaction is carried out to obtain the pyranoquinoline derivative, wherein the catalyst adopts a magnetic nano-material catalyst, and the structuralformula of the pyranoquinoline derivative is described in the specification. By adopting the technical scheme, the utilization rate of reaction raw materials and the product yield are relatively high, the catalytic system can be recycled, the pollution to the environment is reduced, and the product purification process is simple.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a compound containing -NH 2 A method for preparing pharmaceutical intermediate pyranoquinoline derivatives catalyzed by magnetic nanomaterials. Background technique [0002] Pyranoquinoline derivatives are the structural units of many natural products, and have a wide range of biological and pharmacological activities, such as anti-platelet aggregation, anti-cytotoxicity, anti-fungal, anti-estrogen disorder, anti-hypertension, anti-diabetes, etc. In addition, they can also be used as insecticides, antibacterial fungicides, antipyretics, analgesics, antihistamines, and the like. Therefore, the preparation of pyranoquinoline derivatives has attracted extensive attention of pharmaceutical synthesis workers. [0003] As one of pyranoquinoline derivatives, there are currently two main methods for preparing 2-amino-4-arylpyranoquinoline derivatives. The first way is to use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052B01J31/06
CPCC07D491/052B01J31/069B01J31/06B01J2231/4288B01J2231/4205B01J35/33
Inventor 卢华沈建忠
Owner 深圳尚诺生物科技有限公司
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