Abstract
IT has been shown1,2that when picolinic and quinaldinic acids are decarboxylated in the presence of aldehydes and ketones, α-pyridyl and α-quinolyl carbinols of the type Py(Qy).CH(OH).R are produced in good yields (40–80 per cent). The course of this reaction has been formulated in terms of the intermediate formation of α-pyridyl and α-quinolyl anions, which are formally of cyanide ion type1,2. The possibility that the cyanide function might by conjugation be extended to the γ-position has been confirmed recently by Mislow3, who has obtained γ-pyridyl diphenylcarbinol by the decarboxylation of isonicotinic acid in benzophenone. We now report that we have prepared γ-quinolyl diphenylcarbinol, m.p. 247°, from cinchoninic acid and benzophenone in yields of 7–10 per cent; we are developing the reaction as a possible route to quinine analogues.
Similar content being viewed by others
Article PDF
References
Dyson and Hammick, J. Chem. Soc., 1724 (1937).
Ashworth, Daffern and Hammick, J. Chem. Soc., 809 (1939).
J. Amer. Chem. Soc., 69, 2559 (1947).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
BROWN, B., HAMMICK, D. & THEWLIS, B. Production of Quinolyl and Pyridyl Anions during Decarboxylation. Nature 162, 73 (1948). https://doi.org/10.1038/162073b0
Issue date:
DOI: https://doi.org/10.1038/162073b0
This article is cited by
-
Reaction of ethyl quininate derivatives with phenyllithium
Chemistry of Heterocyclic Compounds (1978)
