Letter | Published:

Production of Quinolyl and Pyridyl Anions during Decarboxylation

Nature volume 162, page 73 (10 July 1948) | Download Citation

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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.

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References

  1. 1.

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

  2. 2.

    , and , J. Chem. Soc., 809 (1939).

  3. 3.

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

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Author information

Affiliations

  1. Dyson Perrins Laboratory, University, Oxford. April 15.

    • B. R. BROWN
    • , D. LL. HAMMICK
    •  & B. H. THEWLIS

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DOI

https://doi.org/10.1038/162073b0

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