Check patentability & draft patents in minutes with Patsnap Eureka AI!

Preparation method for quinoline-4-carboxylic acid derivative

A technology of quinoline carboxylic acid and acid anhydride, applied in the field of preparation of quinoline-4-carboxylic acid derivatives, can solve the problem of no quinoline-4-carboxylic acid derivatives, few quinoline-4-carboxylic acid derivatives, etc. problems, achieve the effect of low cost, stable process and mild reaction conditions

Inactive Publication Date: 2013-02-13
湖北欣瑞康医药科技有限公司
View PDF7 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are few synthetic techniques about quinoline-4-carboxylic acid derivatives disclosed in the prior art, only the synthetic method of 2-methyl-3-hydroxyl-6-isopropylquinoline-4-carboxylic acid (patent Application No.: 200510046748.6 and Patent Application No.: 200510048123.3), while there is no research on other quinoline-4-carboxylic acid derivatives

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
  • Preparation method for quinoline-4-carboxylic acid derivative
  • Preparation method for quinoline-4-carboxylic acid derivative
  • Preparation method for quinoline-4-carboxylic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of embodiment 1 2-methylquinoline-4-carboxylic acid

[0034] In a 500ml three-necked flask, add 25g of isatin (0.17mol), 54.4g of sodium hydroxide (1.36mol) and 110ml of water, stir at 25-35°C for 0.5 hours, then add acetone, heat and reflux for 10 hours, cool down, adjust PH=5-6, suction filtration gives 31.5g of 2-methylquinoline-4-carboxylic acid, (C 11 h 9 NO 2 , FW: 187.19), m.p.238-240°C, the yield was 99%.

[0035] 1H-NMR (400MHz, DMSO-d6 / ppm): 8.127 (7, 1H, ddd, J=7.256, J=1.845, J=0.594), 7.692 (8, 1H, ddd, J=7.658, J=7.256, J=1.862), 7.574 (9, 1H, ddd, J=8.323, J=7.658, J=1.845), 8.468 (10, 1H, dddd, J=8.323, J=1.862, J=1.511, J=0.594) , 8.418(13, 1H, d, J=1.511), 2.587(14, 3H).

Embodiment 2

[0036] Example 2 Preparation of 2-vinylphenyl-4-quinolinecarboxylic acid

[0037] Add 7.5g of 2-methylquinoline-4-carboxylic acid (0.04mol) and 24ml of benzaldehyde (0.24mol) into a 250ml three-necked flask, heat up to 100°C for 3 hours, filter, and dry to obtain 2-ethylene as a yellow solid Base-4-quinolinecarboxylic acid monohydrate 10g, (C 18 h 15 NO 3 , FW: 293.32), m.p.294-295°C, yield 85%.

[0038] PMR(d 6 -DMSO): 8.08 (d, 8-H, 3 J 8 -H, 7 -H=8.5Hz), 8.23(s, 3-H), 8.62ppm(d, 5-H, 3 J 5 -H, 6 -H=8.3Hz); Found: C 73.9; H 5.0; N 4.8; H 2 O7.0%.IR: 3345cm -1 (OH), 965cm -1 (C=CH-trans).C 18 h 15 NO 3 .Calculated: C 73.7; H 5.1; N 4.8; H2O 6.1%.

Embodiment 3

[0039] Example 3 2-vinyl-4-quinolinecarboxylic acid

[0040] Add 21g of 2-vinyl-4-quinolinecarboxylic acid monohydrate (0.07mol) and 350ml of acetic anhydride (3.7mol) into a 500ml three-necked flask, heat up to 120°C for 5 hours, filter, and dry to obtain a yellow solid 2-vinyl-4-quinolinecarboxylic acid 18.41g, (C 18 h 13 NO 2 , FW: 275.30672), m.p.295-296°C, the yield was 93.4%.

[0041] IR: 2480cm -1 (OH), 965cm -1 (C=CH-trans).Found: C 78.4; H 4.7; N 4.7%.C 18 h 13 NO 2 .Calculated: C 78.5; H 4.8; N 5.1%.

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 present invention relates to a preparation method for a quinoline-4-carboxylic acid derivative, wherein an isatin derivative is adopted as a starting material, and ring opening, condensation, addition, elimination, oxidation and decarboxylation are performed under a basic condition to obtain the quinoline-4-carboxylic acid derivative. The preparation method has characteristics of cheap and easily-available synthetic raw materials, mild reaction conditions and stable process, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of quinoline-4-carboxylic acid derivatives. Background technique [0002] Quinoline-4-carboxylic acid derivatives, also known as 4-carboxylic acid quinoline derivatives, its general molecular structure formula (I) [0003] [0004] Quinoline-4-carboxylic acid derivatives are important pharmaceutical intermediates and have important applications in the pharmaceutical industry. It is one of the raw materials for the synthesis of drugs such as VLA-4 antagonists, Urotensin II antagonists, tachykinin antagonists, and synthetic antiplatelet aggregation agents. An important intermediate of analgesic and anti-inflammatory drugs such as Xin Kefen. [0005] At present, there are few synthetic techniques about quinoline-4-carboxylic acid derivatives disclosed in the prior art, only the...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/50
Inventor 刘明星吴建宏胡利修
Owner 湖北欣瑞康医药科技有限公司
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com