Alternative and Straightforward Synthesis of Dopaminergic 5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine

Abstract

5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine was synthesized from 2-naphthoic acid in six steps with an overall yield of 27%. Following the reaction sequence, bromination, esterification, substitution with NaOMe in the presence of CuI, the Birch reduction, Curtius rearrangement, and hydrogenolysis afforded biologically active title compound 5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine as hydrogen chloride salt.