Hydrazine hydrate (1:1) → HCID 43446585, compound

Participants

Reaction Steps

A suspension of 1-(2-(dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (320 mg, 1.215 mmol) in dry methanol (10 mL) was treated with Ra—Ni (˜0.05 g) followed by hydrazine hydrate (0.38 mL, 12.2 mmol) at room temperature and the resulting mixture was refluxed for 20 min. The colorless reaction was cooled to room temperature, filtered through a celite pad, washed with methanol (2×10 mL). The combined methanol layer was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95). Yield: 280 mg of colorless oil (98%). 1H NMR (CDCl3) δ: 6.86 (d, J=8.4 Hz, 1H), 6.57 (dd, J=2.7, 8.4 Hz, 1H), 6.51 (d, J=2.1 Hz, 1H), 4.01 (t, J=7.5 Hz, 2H), 2.78 (t, J=7.2 Hz, 2H), 2.58 (t, J=7.2 Hz, 2H), 2.51 (t, J=7.2 Hz, 2H), 2.31 (s, 6H). MS (ESI): 234.2 (M+1).

Provenance & Evidence