Advertisement

Chemistry of Heterocyclic Compounds

, Volume 8, Issue 10, pp 1242–1245 | Cite as

2-Pyridones

VI. Nitration of 6-phenyl-2-pyridone
  • N. P. Shusherina
  • T. I. Likhomanova
Article

Abstract

The nitration of 6-phenyl-2-pyridone with 70% nitric acid, nitronium tetrafluoroborate, and acetyl nitrate has been studied for the first time. It was shown that, depending on the reaction temperature, the nitro group enters the 3 or 5 position of the heterocyclic ring. 3- Nitro-6-(p-nitrophenyl)-2-pyridone is formed by the action of fuming nitric acid on 6-phenyl-2-pyridone. The structures of the nitropyridones obtained were proved by PMR spectroscopy.

Keywords

Spectroscopy Nitrate Organic Chemistry Nitric Acid Reaction Temperature 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    O. Fischer and M. Chur, J. Prakt. Chem., 93, [2], 363 (1916).Google Scholar
  2. 2.
    A. E. Chichibabin and S. A. Shapiro, Zh. Russk. Fiz. Khim. Obshchestva, 53, 233 (1921).Google Scholar
  3. 3.
    A. Albert, J. Chem. Soc., 1020 (1960).Google Scholar
  4. 4.
    E. Klinsberg, Pyridine and Its Derivatives, New York-London (1961), p. 247; (1962), p. 666.Google Scholar
  5. 5.
    A. Burton, P. Halls, and A. Katritzky, Tet. Letters, 2211 (1971).Google Scholar
  6. 6.
    N. P. Shusherina, N. D. Dmitrieva, E. A. Luk'yanets, and R. Ya. Levina, Zh. Obshch. Khim., 33, 3434 (1963).Google Scholar
  7. 7.
    L. Paquette and W. Farley, J. Org. Chem., 32, 2725 (1967).Google Scholar
  8. 8.
    H. Hertog, D. Burman, and P. Villiers, Rec. Trav. Chim., 80, 325 (1961).Google Scholar
  9. 9.
    F. Broekmann and H. Tandelloo, Rec. Trav. Chim., 81, 107 (1962).Google Scholar
  10. 10.
    K. Schofield, Quart. Rev., 4, 382 (1950).Google Scholar
  11. 11.
    R. Selms, J. Org. Chem., 33, 478 (1968).Google Scholar
  12. 12.
    L. D. Smirnov, M. P. Avezov, V. P. Lezina, B. E. Zaitsev, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, 845 (1971).Google Scholar
  13. 13.
    C. Bonsall and J. Hill, J. Chem. Soc., C, 1836 (1967).Google Scholar
  14. 14.
    W. Pirkle and M. Dines, J. Heterocycl. Chem., 6, 1 (1969).Google Scholar
  15. 15.
    J. Leben, Ber., 29, 1675 (1896).Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • N. P. Shusherina
    • 1
  • T. I. Likhomanova
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityUSSR

Personalised recommendations