Acetic acid--water (1/1) → Tetralin

Participants

Reaction Steps

To 7-nitro-2-((phenylmethyl)(methyl)amino)-1,2,3,4-tetrahydronaphthalene hydrochloride (0.89 g, 2.7 mmol) in 85% AcOH/H2O (75 ml) was added zinc metal (3.5 g, 54.0 mmol). The mixture was stirred for 5 min, filtered through celite, and evaporated to an oil. The oil was dumped into basic water and extracted with chloroform (3×20 ml). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated to an oil. Treatment with IPA/HCl yielded 7-amino-2-((phenyl)methyl)(methyl)amino)-1,2,3,4-tetrahydronaphthalene: (0.81 g, 88%); M.S. (M+H)+ =267.

Provenance & Evidence