Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing 6-hydroxyl-3,4dihydro-2(1H)-quinolinone

A technology of quinolinone and dihydro, which is applied in the field of preparation of 6-hydroxy-3,4dihydro-2(1H)-quinolinone, can solve problems such as high cost, high viscosity of the system, and environmental pollution, and achieve Ease of control, improvement of product yield and quality, and avoidance of the use of organic solvents

Inactive Publication Date: 2009-03-25
BEIJING D VENTUREPHARM TECH DEV
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The second process is the deprotection reaction, which needs to be reacted at 150-200°C. Although compound (II) can be melted at about 120°C, the above-mentioned high-viscosity complex and unreacted trichloride still exist in the system at this time. Aluminum chloride makes the system very viscous and cannot continue to react. The viscosity of the system can be slightly reduced by rapid temperature rise, but aluminum trichloride will sublimate at about 180°C, and it still cannot be stirred normally.
[0008] The nitrification, reduction and other processes involved in the reaction process of this method are not easy to control, and a large amount of waste is produced, the yield of the reaction is low, the cost is high, and the environmental pollution is relatively serious

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing 6-hydroxyl-3,4dihydro-2(1H)-quinolinone
  • Method for preparing 6-hydroxyl-3,4dihydro-2(1H)-quinolinone
  • Method for preparing 6-hydroxyl-3,4dihydro-2(1H)-quinolinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 10g (0.05mol) of the compound of formula II, 25g (0.19mol) of aluminum trichloride, and 7.10g (0.12mol) of sodium chloride into a 250mL three-neck flask, mix well, stir mechanically, heat up to 160-170°C and keep it warm for 2 hours , cooled to 60°C, added a mixture of 50mL of concentrated hydrochloric acid and 100g of crushed ice, stirred slowly, a brick red solid precipitated, cooled to room temperature, filtered with suction, washed with pure water until neutral to obtain a crude product. The above crude product was recrystallized with ethanol and decolorized with activated carbon to obtain 6.2 g of off-white crystals of the compound of formula I with a yield of 81.2%.

Embodiment 2

[0021] Add 250g (1.17mol) of the compound of formula II, 624g (4.68mol) of aluminum trichloride, and 177g (3.04mol) of sodium chloride into a 5L three-neck flask, mix well, stir mechanically, heat up to 170-180°C and keep it warm for 2 hours. Cool down to 140°C, slowly pour the system into a mixture of 1250mL concentrated hydrochloric acid and 2500g crushed ice, stir slowly, a brick-red solid precipitates, cool to room temperature, filter with suction, wash with pure water until neutral, and obtain a crude product. The above crude product was recrystallized with ethanol and decolorized with activated carbon to obtain 168.0 g of off-white crystals of the compound of formula I with a yield of 88.0%.

Embodiment 3

[0023] Add 10g (0.05mol) of the compound of formula II, 25g (0.19mol) of aluminum trichloride, and 8.95g (0.12mol) of potassium chloride into a 250mL three-neck flask, mix well, stir mechanically, heat up to 160-170°C and keep it warm for 2 hours , cooled to 60°C, added a mixture of 50mL of concentrated hydrochloric acid and 100g of crushed ice, stirred slowly, a brick red solid precipitated, cooled to room temperature, filtered with suction, washed with pure water until neutral to obtain a crude product. The above crude product was recrystallized with ethanol and decolorized with activated carbon to obtain 6.1 g of off-white crystals of the compound of formula I with a yield of 79.4%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a method for preparing 6-hydroxy-3, 4 dihydro-2(1H)-quinolone (compound of formula I), and the compound is a key intermediate in the pharmaceutical and chemical field.

Description

technical field [0001] The present invention relates to the preparation method of formula (I) compound 6-hydroxy-3,4-dihydro-2(1H)-quinolinone, which is an important intermediate in the field of medicine and chemical industry. Background technique [0002] 6-Hydroxy-3,4-dihydro-2(1H)-quinolinone is a synthetic antithrombotic agent, antithrombinase agent, agent for treating cerebral circulation disorder, coronary artery vasodilator, phosphodiesterase inhibitor, adrenal gland Important pharmaceutical intermediates and organic chemical raw materials such as blockers, sedatives, nerve stabilizers, platelet aggregation inhibitors and antibacterial agents. In addition, it can also be used in the synthesis of herbicides in agriculture. [0003] It is known that this compound can be synthesized by the following two routes, the first route: [0004] [0005] This reaction includes two processes. The first process is to form a ring through the intramolecular Friedel-Crafts alkyla...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D215/227
Inventor 张宏涛谌伦华焦育红
Owner BEIJING D VENTUREPHARM TECH DEV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products