Letter | Published:

Oxidation of Neostrychnine

Nature volume 160, page 18 (05 July 1947) | Download Citation

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Abstract

The action of bromine on neostrychnine, C21 H22 O2 N2, in cold acid solution affords a bromo-hydrobromide transformed by hot water into the hydrobromide of oxodihydroallostrychnine (formerly called oxodihydroneostrychnine), C21 H22 O3 N2, in nearly theoretical yield. This substance has now been recognized as an aldehyde, and its formation involves a molecular rearrangement,: N.CH = C: →: N—C(CHO):. It is noteworthy that the reverse transformation can be realized. Catalytic reduction of the aldehyde in alcoholic solution gives a dihydro-derivative, probably the related primary alcohol; in acetic acid solution an isomeride is produced in addition, and this is converted with great ease by dilute mineral acids into neostrychnine. Nitrous acid transforms neostrychnine into a ketoxime-formamide,: N.CH: C: →: N.CHO HON: C:, which is hydrolysed by dilute hydrochloric acid to hydroxylamine, formic acid and a hydrochloride, C20 H23 O3 N2 Cl. This is a salt of a sec-basic ketone.

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References

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    , Nature, 159, 263 (1947).

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    , Experientia, ii, 1, 28 (1946). , , and , J. Chem. Soc., 903 (1946).

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Affiliations

  1. Dyson Perrins Laboratory, South Parks Road, Oxford. May 19.

    • R. N. CHAKRAVARTI
    •  & R. ROBINSON

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DOI

https://doi.org/10.1038/160018a0

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