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

A kind of preparation method of quinoline-2-carboxylate series

A formate and series technology, which is applied in the field of preparation of quinoline-2-formate series, can solve the problems of high temperature and harsh reaction conditions, and achieve the effects of simple operation, less side reactions and good application prospects

Active Publication Date: 2021-06-11
JIANGXI NORMAL UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the development of the above method provides an effective method for the synthesis of quinoline-2-formic acid ester series, some reaction conditions are relatively harsh, and the temperature is too high, which limits some functional group substrates. Therefore, a more effective method is developed to synthesize quinoline Phenyl-2-carboxylate derivatives have very important theoretical research value and practical significance in industrial production

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
  • A kind of preparation method of quinoline-2-carboxylate series
  • A kind of preparation method of quinoline-2-carboxylate series
  • A kind of preparation method of quinoline-2-carboxylate series

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0016]

[0017] In a 25mL Schlenk reaction tube equipped with a magnetic stirring bar, add 2-isopropenylaniline (0.2mmol, 1.0eq.), rhodium acetate (0.01mmol, 5mol%), copper acetate (0.4mmol, 2.0eq. ), sodium carbonate (0.4mmol, 2.0eq.), 1,2-dichloroethane (2mL) and diethyldiazomalonate (0.4mmol, 2.0eq.). The reaction tube was placed in a heating module at 100° C., and reacted for 24 hours. TLC detected that the reaction was complete. The reaction solution was cooled to room temperature, and after adding 10 mL of ethyl acetate, the catalyst was filtered through a short column of silica gel to remove the catalyst, transferred to a 50 mL round bottom flask, added a small amount of silica gel, spin-dried, and the crude product was separated and purified by flash column chromatography to obtain 4 -Methylquinoline-2-carboxylic acid ethyl ester (formula a), yield 76%. 1 H NMR (400MHz, CDCl 3 )δ8.32(d, J=8.1Hz, 1H), 8.05(d, J=4.4Hz, 2H), 7.78(t, J=7.2Hz, 1H), 7.68(t, J=8.0Hz, 1H)...

example 2

[0019]

[0020]In a 25mL Schlenk reaction tube equipped with a magnetic stir bar, add 2-isopropenyl-6-fluoroaniline (0.2mmol, 1.0eq.), rhodium acetate (0.01mmol, 5mol%), copper acetate (0.4mmol , 2.0eq.), sodium carbonate (0.4mmol, 2.0eq.), 1,2-dichloroethane (2mL) and diethyldiazomalonate (0.4mmol, 2.0eq.). The reaction tube was placed in a heating module at 100° C., and reacted for 24 hours. TLC detected that the reaction was complete. The reaction solution was cooled to room temperature, and after adding 10 mL of ethyl acetate, the catalyst was filtered through a short column of silica gel to remove the catalyst, transferred to a 50 mL round bottom flask, added a small amount of silica gel, spin-dried, and the crude product was separated and purified by flash column chromatography to obtain 4 -Methyl-8-fluoroquinoline-2-carboxylic acid ethyl ester (formula b), yield 65%.

[0021] 1 H NMR (400MHz, CDCl 3 )δ8.32(dd, J=9.2, 5.6Hz, 1H), 8.06(s, 1H), 7.63(dd, J=9.7, 2.6Hz,...

example 3

[0023]

[0024] In a 25mL Schlenk reaction tube equipped with a magnetic stir bar, add 2-isopropenyl-5-fluoroaniline (0.2mmol, 1.0eq.), rhodium acetate (0.01mmol, 5mol%), copper acetate (0.4mmol , 2.0eq.), sodium carbonate (0.4mmol, 2.0eq.), 1,2-dichloroethane (2mL) and diethyldiazomalonate (0.4mmol, 2.0eq.). The reaction tube was placed in a heating module at 100° C., and reacted for 24 hours. TLC detected that the reaction was complete. The reaction solution was cooled to room temperature, after adding 10 mL of ethyl acetate, the catalyst was removed by suction filtration through a short column of silica gel, transferred to a 50 mL round bottom flask, a small amount of silica gel was added, spin-dried, and the crude product was separated and purified by flash column chromatography to obtain Ethyl 4-methyl-7-fluoroquinoline-2-carboxylate (formula c), yield 65%.

[0025] 1 H NMR (400MHz, CDCl 3 )δ8.05(dd, J=9.2, 5.9Hz, 1H), 8.00(s, 1H), 7.94(dd, J=10.0, 2.4Hz, 1H), 7.46(...

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 a preparation method of quinoline-2-carboxylate series. It adopts 2-alkenylaniline as a reaction substrate, under the action of a transition metal rhodium catalyst, a base, and an oxidizing agent, heats and stirs with diazomalonate in an organic solvent to obtain quinoline-2-formic acid ester series. The preparation method of the invention has mild reaction conditions, simple and convenient operation, low cost, few side reactions, high product purity, and is convenient for separation and purification. The product structure obtained by the present invention is 1 H NMR, 13 C NMR, HRMS and other characterization confirmation. The method provided by the invention provides a new approach for the synthesis of important raw materials (quinoline-2-formic acid ester derivatives) of fine chemicals. In addition, this method is beneficial to industrial production, and the product has potential biological and pharmaceutical activities, and is widely used in the fields of biological or pharmaceutical active molecules, pesticides and medicine, and can also be used as an intermediate to further synthesize more complex compounds, which has a very good application prospect.

Description

technical field [0001] The invention relates to quinoline series compounds, in particular to a preparation method of quinoline-2-carboxylate series. Background technique [0002] Quinoline series compounds are a class of important nitrogen-containing heterocyclic compounds, and have good biological and pharmacological activities ((a) Andries, K.; Verhasselt, P.; Guillemont, J.; Gohlmann, H.W.H.; Neefs, J.; Winkler, H.; Gestel, J.V.; Timmerman, P.; Zhu, M.; E.; Truffot-Pernot, C.; Lounis, N.; Jarlier, V. Science 2005, 307, 223; (b) Bax, B.D.; Chan, P.F.; Eggleston, D.S.; , F.; Giordano, I.; Hann, M.M.; Hennessy, A.; Hibbs, M.; Huang, J.; Jones, E.; Jones, J.; Brown, K.K.; Lewis, C.J.; May, E.W.; Saunders, M.R.; Singh, O.; spitzfaden, C.E.; Shen, C.; Suhillings, A.; Theobald, A.J.; Wohlkonig, A.; Pearson, N.D.; Gwynn, M.N. Nature 2010, 466, 935.). Quinoline compounds have been widely used in the field of medicine. For example, mefloquine, chloroquine, and amodiaquine are r...

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 Patents(China)
IPC IPC(8): C07D215/48
CPCC07D215/48
Inventor 丁秋平郑强王聪彭以元
Owner JIANGXI NORMAL UNIV
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