Russian Journal of Organic Chemistry

, Volume 41, Issue 5, pp 772–773 | Cite as

Synthesis and Transformations of 4-(4-Ethoxycarbonylphenylamino)- and 4-(2-Carboxyphenylamino)quinolines

  • A. A. Avetisyan
  • I. L. Aleksanyan
  • L. P. Ambartsumyan


Synthesis was performed of 4-(4-ethoxycarbonylphenylamino)- and 4-(2-carboxyphenylamino)-2-methylquinolines by reaction of 2-methyl-4-chloroquinoline with anesthesin and anthranilic acid. In concentrated sulfuric acid 4-(2-carboxyphenylamino)-2-methylquinoline underwent cyclization into 6-hydroxy-7-methylquinolino[3,2-c]quinoline, and the alkaline hydrolysis of 4-(4-ethoxycarbonylphenyl-amino)quinoline afforded 2-methyl-4-(4-carboxyphenylamino)quinoline.


Hydrolysis Organic Chemistry Sulfuric Acid Quinoline Alkaline Hydrolysis 


  1. 1.
    Mashkovskii, P.P.M., Drugs, Moscow: Novaya Volna, 2002, vol. 2, p. 336.Google Scholar
  2. 2.
    Fitch, C.D., Life Sciences, 2004, vol. 74, p. 1957.PubMedGoogle Scholar
  3. 3.
    Wainwright, M. and Kristasen, J.E., Intern. J. Antimicrob. Agents, 2003, vol. 22, p. 479.Google Scholar
  4. 4.
    Taramelli, D., Tognazioli, C., Ravagnani, F., Leopardi, O., Giannuis, G., and Boelaert, J.R., Antimicrob. Agents, Chemother., 2001, vol. 45, p. 1450.Google Scholar
  5. 5.
    Boshelli, D.H., Fei, Ye, Wang, Y.D., Dutia, M., Johnson, S.L., Bigi, Wu, Miller, K., Powell, D.W., Yaczko, D.,, Young, M., Tischer, M., Arndt, K., Diseafani, C., Etienne, C., Crod, J., Lucas, J., Weber, J.M., Boschelli, F., and Gibbons, J., J. Med. Chem., 2001, vol. 44, p. 3965.PubMedGoogle Scholar
  6. 6.
    Berger, D., Dutia, M., Poweli, D., Wissner, A., DeMorin, F., Raifeld, Y., Weber, J., and Boschelli, F., Bioorg. &, Med. Chem. Lett., 2002, vol. 12, p. 2989.Google Scholar
  7. 7.
    Berger, D., Dutia, M., Powell, D., Bigi, Wu, Wissner, A., DeMorin F., Weber, J., and Boschelli, F., Bioorg. & Med. Chem. Lett., 2002, vol. 12, p. 2761.Google Scholar
  8. 8.
    Liach, C.A. and Brown, T.N., Europe Patent 330485, 1990; Chem. Abstr., 1990, vol. 112, 158073s.Google Scholar
  9. 9.
    Geiss, K.H., Rucbsamen, K., and Traut, M., Europe Patent 387821, 1990; Chem. Abstr., 1991, vol. 114, 112074v.Google Scholar
  10. 10.
    Beilst. H., vol. 20, p. 392.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • A. A. Avetisyan
    • 1
  • I. L. Aleksanyan
    • 1
  • L. P. Ambartsumyan
    • 1
  1. 1.Yerevan State UniversityYerevanArmenia

Personalised recommendations