2-(1-Methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline → 2-(1-Methylethyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine

Participants

Reaction Steps

2-(1-methylethyl)-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (0.24 g, 0.94 mmol) was dissolved in ethyl acetate (5 mL), treated with 10% palladium on carbon (50 mg, Aldrich), and then diluted with methanol (10 mL). The mixture was stirred under 60 psi of hydrogen pressure for 16 h in a Fischer-Porter apparatus. The pressure was released, the reaction vessel evacuated, and back-filled with nitrogen twice. The mixture was filtered through celite and the filtrate was concentrated to provide 2-(1-methylethyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine (206 mg, 0.94 mmol, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 1.13 (d, J=6.6 Hz, 6 H), 2.71-2.81 (m, 4 H), 2.87 (tt, J=6.5, 6.5 Hz, 1 H), 3.59 (s, 2 H), 3.63 (bs, 2 H), 3.81 (s, 3 H), 6.40 (s, 1 H), 6.50 (s, 1 H).

Provenance & Evidence