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KMID : 0043319840070020081
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Archives of Pharmacal Research
1984 Volume.7 No. 2 p.81 ~ p.85
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Transformation of 5,6-Dimethoxy-2-amino-1-tetralol Hydrochloride into 5,6-Dimethoxy-2-tetralone
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Kim JC
Park WW/Kim MS/Yoon UC/Shin HD/Koh YS
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Abstract
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The reduction procedure of 5,6-dimethoxy -2-amino-l-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 rearrangement was verified on the basis of IR, NMR and the result of elemental analysis. A plausible mechanism for the rearrangement is discussed.
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