Jack C. Kim, W. Park, Min-Sook Kim
Dec 1, 1984
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Journal
Archives of Pharmacal Research
Abstract
The reduction procedure of 5,6-dimethoxy-2-amino-1-tetralone with sodium bis-(2-methoxy)-aluminum hydride, followed by palladium on charcoal in the presence of HClO4 gave a major reduction product of 5,6-dimethoxy-2-amino-tetralin, along with a small amount of a transformed 5,6-dimethoxy-2-tetralone. The isolated intermediate, 5,6-dimethoxy-2-amino-1-tetralol hydrochloride yielded exclusively 5,6-dimethoxy-2-tetralone under catalytic acidic conditions (acid treatment). The unusual rearangement was verified on the basis of IR, NMR and the result of elemental analysis. A plausible mechanism for the rearrangement is discussed.