Method A. As outlined in Scheme I either 3, 5-dimethoxybenzamide (2) or 3, 4, 5- trimethoxybenzamide (3) gave rise to the same compound: 3-carbamoyl-1, Ei-di-methoxy-l, 4-cyclohexadiene (4) when submitted to a Birch reduction under classical conditions. 12 A further reduction of the carboxamide 4 with lithium aluminum hydride (LAH) in tetrahydrofuran led to an approximate 1: l mixture of the expected 3-(aminomethyl)-l, 5- ...
