Hydrazine hydrate (1:1) → HCID 53392453, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N,N-dimethyl-3-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)propan-1-amine (600 mg, 2.278 mmol) in methanol (12 ml) was added Raney nickel (60 mg, 2.278 mmol) followed by hydrazine hydrate (1.108 ml, 22.78 mmol). The resulting mixture was then stirred at 60° C. and monitored by TLC for consumption of the starting material. The reaction mixture was then filtered through celite and the filtrate was concentrated. The residue was then dissolved in dichloromethane, dried, filtered and concentrated to give a dark oil. 1H NMR (DMSO-d6) δ 6.37-6.34 (m, 1H), 6.30-6.26 (m, 1H), 6.22-6.20 (m, 1H), 4.17 (brs, 2H), 3.12-3.03 (m, 4H), 2.55 (t, J=6.45 Hz, 2H), 2.20 (t, J=6.9 Hz, 2H), 2.11 (s, 6H), 1.79 (quint, J=6 Hz, 2H), 1.56 (quint, J=7.12 Hz, 2H). ESI-MS (m/z, %) 234 (MH+, 100), 161 (60).

Provenance & Evidence