Production of Quinolyl and Pyridyl Anions during Decarboxylation

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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.

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  1. 1

    Dyson and Hammick, J. Chem. Soc., 1724 (1937).

  2. 2

    Ashworth, Daffern and Hammick, J. Chem. Soc., 809 (1939).

  3. 3

    J. Amer. Chem. Soc., 69, 2559 (1947).

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BROWN, B., HAMMICK, D. & THEWLIS, B. Production of Quinolyl and Pyridyl Anions during Decarboxylation. Nature 162, 73 (1948) doi:10.1038/162073b0

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