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

Environmental-friendly and efficient preparation method of quinolone compound

A compound and quinolone technology, which is applied in the field of green and efficient preparation of quinolone compounds, can solve the problems of complex synthesis process, limited scope of use, and great environmental harm, and achieve the effects of good product diversity, low cost and high yield

Inactive Publication Date: 2015-01-07
YUNNAN MINZU UNIV
View PDF2 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the complex synthesis process and high cost of this type of compound, the production process is harmful to the environment, which limits its application range.

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1. Preparation of 4-oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester

[0026] 30 mg of aniline was placed in a 15 mL reaction test tube, 51 mg of diethyl butynedate was added dropwise at room temperature, stirred and mixed, and reacted at room temperature for 0.5 h. The reactant was monitored by TLC spot plate. After the reaction, the reaction solution was subjected to silica gel column chromatography, and concentrated by rotary evaporation under reduced pressure to obtain the target product as a yellow oil. After that, the product was placed in a round-bottomed flask and 0.5 mL of catalyst was added. The mixture was heated and stirred in an oil bath at 90 °C for 1 h, and monitored by TLC. After the reaction was completed, the catalyst was quenched with ice water, and then dichloromethane was added. Extraction, the extract was dehydrated with anhydrous sodium sulfate, and then concentrated and recrystallized by rotary evaporation under reduced pressure ...

Embodiment 2

[0027] Embodiment 2. Preparation of 6-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester

[0028] 32 mg of p-methylaniline was placed in a 15 mL reaction test tube, 51 mg of diethyl butynedioate was added dropwise at room temperature, stirred and mixed, and reacted at room temperature for 0.5 h. The reactant was monitored by TLC spot plate. After the reaction, the reaction solution was subjected to silica gel column chromatography, and concentrated by rotary evaporation under reduced pressure to obtain the target product as a yellow oil. After that, the product was placed in a round-bottomed flask and 0.5 mL of catalyst was added. The mixture was heated and stirred in an oil bath at 90 °C for 1 h, and monitored by TLC. After the reaction was completed, the catalyst was quenched with ice water, and then dichloromethane was added. Extraction, the extract was dehydrated with anhydrous sodium sulfate, and then concentrated and recrystallized by rotary evaporation unde...

Embodiment 3

[0029] Example 3. Preparation of ethyl 6-methoxy-4-oxo-1,4-dihydroquinoline-2-carboxylate

[0030] 37 mg of p-methoxyaniline was placed in a 15 mL reaction test tube, 51 mg of diethyl butynedioate was added dropwise at room temperature, stirred and mixed, and reacted at room temperature for 0.5 h. The reactant was monitored by TLC spot plate. After the reaction, the reaction solution was subjected to silica gel column chromatography, and concentrated by rotary evaporation under reduced pressure to obtain the target product as a yellow oil. After that, the product was placed in a round-bottomed flask and 0.5 mL of catalyst was added. The mixture was heated and stirred in an oil bath at 90 °C for 1 h, and monitored by TLC. After the reaction was completed, the catalyst was quenched with ice water, and then dichloromethane was added. Extraction, the extract was dehydrated with anhydrous sodium sulfate, and then concentrated and recrystallized by rotary evaporation under reduced p...

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 discloses an environmental-friendly and efficient preparation method of a quinolone compound. According to the adopted technical scheme, the environmental-friendly and efficient preparation method comprises the following steps: putting an intermediate 1 (I) in a reactor, dropwise adding an intermediate 2 (II) at a room temperature, and mixing and stirring uniformly under the condition without solvent to carry out solvent-free hydroamination; after a detection reaction is completed, carrying out chromatography on reaction liquid through a silicagel column, concentrating through reduced pressure distillation to obtain a yellow oily intermediate 3 (III); then putting the intermediate 3 (III) in the reactor, directly adding a catalyst, heating for dissolution while stirring to carry out an intramolecular cyclization reaction; after the detection reaction is completed, quenching the reaction by using ice water, extracting, concentrating and recrystallizing to obtain a target compound 4 (IV). The preparation method of the quinolone compound disclosed by the invention is environmental-friendly, efficient, simple, convenient and safe to operate, and the produced quinolone compound is low in cost.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a green and efficient preparation method of quinolone compounds. Background technique [0002] Quinolones are a class of chemically synthesized drugs widely used in clinical anti-infection. They have the characteristics of broad-spectrum, high efficiency, and low toxicity. Representative drugs ofloxacin, ciprofloxacin, enrofloxacin, and gatifloxacin are widely used clinically. Many pharmaceutical companies at home and abroad are competing to develop and produce such drugs. However, due to the complex synthesis process and high cost of this type of compound, the production process is harmful to the environment, which limits its application range. If the synthesis process can be improved, it will help to reduce the cost and reduce pollution, and expand the scope of its clinical application. Contents of the invention [0003] The present invention is just to overcome the above-...

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): C07D215/48
CPCC07D215/48C07C209/60C07C213/00C07C211/45C07C211/52C07C217/84
Inventor 黄超郭家辉尹艳清袁明龙杨丽娟郭俊明
Owner YUNNAN MINZU UNIV
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

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com