Unusual Transposition of the Carbonyl Group in the Reduction of 2-Amino-1-indanone

Article abstract of DOI:10.1246/bcsj.54.3197

The catalytic reduction procedure of 2-amino-4,5-dimethoxy-1-indanone hydrochloride gave a major reduction product of 2-amino-4,5-dimethoxyindan hydrochloride, along with a small amount of a rearranged 4,5-dimethoxy-2-indanone.The isolated intermediate, 2-amino-4,5-dimethoxy-1-indanol hydrochloride yielded exclusively 4,5-dimethoxy-2-indanone under catalytic reaction conditions (acid treatment).The unusual transformation product was verified on the basis of IR, NMR and the result of elemental analysis.A plausible mechanism for the rearrangement is discussed.