Chemistry of Heterocyclic Compounds

, Volume 16, Issue 3, pp 275–277 | Cite as

Synthesis and bromination of 8-methylquinoline-5-carboxylic acid

  • I. N. Gracheva
  • A. I. Tochilkin


8-Methylquinoline-5-carboxylic acid was obtained by the Skraup reaction from 3-amino-p-toluic acid or by hydrolysis of 5-cyano-8-methylquinoline. The latter was synthesized by the Rosenmund-von Braun reaction from 5-bromo-8-methylquinoline, which was obtained by bromination of 8-methylquinoline in the presence of silver sulfate. Bromination in the side chain of 8-methylquinoline-5-carboxylic acid and its nitrile was studied.


Sulfate Hydrolysis Organic Chemistry Nitrile Silver Sulfate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    K. K. Shatemirova, G. A. Davydova, I. V. Verevkina, and A. I. Tochilkin, Vopr. Med. Khim., 23, 609 (1977).Google Scholar
  2. 2.
    W. Miller, Ber., 23, 2262 (1890).Google Scholar
  3. 3.
    E. Lellman and H. Alt, Ann., 237, 308 (1887).Google Scholar
  4. 4.
    G. I. Mikhailov, Tr. IREA, 18, 51 (1941).Google Scholar
  5. 5.
    Ya. I. Gur'yan and Yu. A. Vakhrushev, Zh. Anal. Khim., 16, 485 (1961).Google Scholar
  6. 6.
    P. B. D. De la Mare, M. Kiamud-din, and J. H. Ridd, J. Chem. Soc., 561 (1960).Google Scholar
  7. 7.
    H. Gilman and S. M. Spatz, J. Am. Chem. Soc., 63, 1553 (1941).Google Scholar
  8. 8.
    O. Werner and F. Vögtle, Synthesis, 4, 272 (1977).Google Scholar
  9. 9.
    J. N. Ospenson, Acta Chem. Scand., 4, 1351 (1950).Google Scholar
  10. 10.
    G. Ganguli, J. Indian Chem. Soc., 11, 197 (1934).Google Scholar
  11. 11.
    T. Ukai, S. Hashimoto, and M. Higashi, J. Pharm. Soc. Jpn., 48, 371 (1928).Google Scholar

Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • I. N. Gracheva
    • 1
  • A. I. Tochilkin
    • 1
  1. 1.Institute of Biological and Medicinal ChemistryAcademy of Medical Sciences of the USSRMoscow

Personalised recommendations