2-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline → 2-Methyl-1,2,3,4-tetrahydroisoquinolin-7-amine

Participants

Reaction Steps

2-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (3.0 g, 15.6 mmol) was dissolved in EtOAc (10 mL) and stirred vigorously with 10% Pd/C (0.3 g) under a hydrogen atmosphere at 55 PSI. The reaction was stirred for 15 h at rt. The reaction was filtered through celite and concentrated to provide 2.2 g (87%) of the desired 2-methyl-1,2,3,4-tetrahydro-7-isoquinolinamine product as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 6.83 (d, J=8.3 Hz, 1H), 6.44 (d, J=8.0 Hz, 1H), 6.24 (s, 1H), 4.97 (s, 2H), 3.87 (m, 2H), 3.11 (t, J=6.4 Hz, 2H), 2.85-2.68 (m, 2H), 2.58 (s, 3H).

Provenance & Evidence