反应详情

6-nitro-1-(3-(piperidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (98 mg, 0.309 mmol) in dry methanol (5 mL) was treated with Ra—Ni (˜0.05 g slurry in water) followed by hydrazine hydrate (96 uL, 3.08 mmol) at room temperature and the resulting mixture was refluxed for 30 minutes. The reaction was cooled to room temperature, filtered through a celite bed, 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, 2.5:97.5). Yield: 71 mg of yellow oil (80%). 1H NMR (CDCl3) δ: 6.90 (d, J=8.4 Hz, 1H), 6.55 (dd, J=2.7, 8.4 Hz, 1H), 6.51 (d, J=2.1 Hz, 1H), 3.91 (m, 2H), 2.80-2.76 (m, 2H), 2.61-2.56 (m, 2H), 2.38-2.33 (m, 6H), 1.84-1.79 (m, 2H), 1.60-1.55 (m, 4H), 1.46-1.42 (m, 2H). MS (ESI): 288.2 (M+1).

1. temperaturethe resulting mixture was refluxed for 30 minutes
2. filtrationfiltered through a celite bed
3. washwashed with methanol (2×10 mL)
4. customThe combined methanol layer was evaporated
5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5)