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Chlorination and hydrochlorination of vinyloxy derivatives of pyridine and quinoline series

Conclusions

  1. 1.

    The corresponding hydrochlorides were obtained by the reaction of 2-vinyloxypyridine, 2-vinyl-oxylepidine, N-vinyl-2-pyridone, N-vinyl-2-lepidone, and 8-vinyloxyquinoline with hydrogen chloride.

  2. 2.

    Chlorine adds to the vinyl derivatives of hydroxypyridine and hydroxyquinoline predominantly across the double bond of the vinyl group, with the formation ofα,β-dichloroethyloxypyridines and pyridones. The reaction is accompanied by side processes.

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Literature cited

  1. 1.

    E. Klingsberg, Pyridine and Its Derivatives, Vol. 3, New York-London (1962).

  2. 2.

    F. L. Kolodkin, Dissertation [in Russian], Moscow (1966).

  3. 3.

    M. A. S. Chaudri, R. D. Desai, and R. F. Hunter, J. Indian Chem. Soc.,11, 249 (1934).

  4. 4.

    P. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems [Russian translation], Mir (1968), pp. 94, 131.

  5. 5.

    J. R. Shelton and L. H. Lee, J. Org. Chem.,25, 428 (1960).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1774–1779, August, 1971.

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Skvortsova, G.G., Tyrina, S.M., Kim, D.G. et al. Chlorination and hydrochlorination of vinyloxy derivatives of pyridine and quinoline series. Russ Chem Bull 20, 1664–1668 (1971). https://doi.org/10.1007/BF00860024

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Keywords

  • Hydrogen
  • Chloride
  • Chlorine
  • Pyridine
  • Double Bond