Isomerism of the Related Compounds of Ephedrine. I

Abstract

p-Methoxy-nor-ephedrine was obtained by the condensation of anisaldehyde, nitroethane and KHCO₃ and subsequent reduction with Fe or Zn and dil. H₂SO₄. Formation of normal and iso compounds was at a ratio of 1:3. Treatment of α-bromo-p-methoxypropiophenone with K-phthalimide and subsequent saponification gave aminoketone hydrochloride, m.p. 216°, which yielded a normal base when catalytically reduced with Adams' PtO₂⋅H₂. It was found that the reduction of anetholnitrosite with Zn+AcOH gives a normal compound, proving that the compound obtained earlier by Krámli and Bruckner by electrolytic reduction of acetyl anetholnitrosite and subsequent heating with 2N-HCl is an iso-form compound since saponification of acylamino-alcohol with mineral acid results in the conversion of normal to the iso compound.