Hydrazine hydrate (1:1) → HCID 57701025, compound

Participants

Reaction Steps

To a solution of tert-butyl methyl(3-(5-nitro-1H-indol-3-yl)cyclohexyl)carbamate (0.70 g 1.87 mmol) in dry MeOH (15 mL) was added Raney-Ni (0.1 g as a slurry in water) and hydrazine hydrate (1.00 mL, 18.70 mmol). The resulting mixture was immersed in a preheated oil bath and refluxed for 15 min. or until the solution became clear. The reaction was cooled and filtered trough Celite, washed with MeOH (20 mL) and the solvent evaporated. The crude was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98) to give the title compound as a light brown solid (0.60 g, 92%). 1H-NMR (CDCl3) δ 1.42 (s, 9H), 1.46-1.72 (m, 6H), 1.88 (ddd, 1H, J=5.4, 12.3, 24.9 Hz), 2.05-2.16 (m, 2H), 2.76 (s, 3H), 3.50 (s, 2H, NH), 4.36-4.51 (m, 1H), 6.64 (dd, 1H, J=2.1, 8.4 Hz), 6.89 (d, 1H, J=2.1 Hz), 7.16 (d, 1H, J=8.4 Hz), 7.28 (s, 1H), 7.76 (s, 1H, NH); EI-MS (m/z, %) 343 (M+, 70), 212 (100).

Provenance & Evidence