Studies on the Syntheses of Isoquinoline Derivatives. I

Syntheses of 1-Ethylhydrohydrastinine and 1-Phenyl-nor-hydrastinine

Abstract

Piperonalmethyl ethyl ketone was prepared from piperonal and the double bond in piperonalmethyl ethyl ketone was reduced through electrolytic hydrogenation. Oxime of this reduced piperonylmethyl ethyl ketone was rearranged with P₂O₅ in toluene by means of Beckmann's rearrangement when 1-ethyl-nor-hydrastinine was formed, at the same time, by Bischler and Napieralsky's method. Methiodide of this compound, obtained by CH₃I, was converted into methochloride by AgCl which was catalytically hydrogenated to 1-ethyl-hydro-hydrastinine.
The previous report on the melting point of piperonylacetophenone has been corrected by the authors. 1-Phenyl-nor-hydrastinine prepared recently by the authors was reconfirmed with the reduced product, constants of which correspond to those appearing in literature.