Ammonia → HCID 53392181, compound

Participants

Reaction Steps

A solution of 6-nitro-1-(2-(piperidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.65 mmol) in 10 mL methanol was added to Raney Nickel (slurry in H2O, 50 mg) in a round bottom flask. The suspension was heated at reflux for 10 minutes then filtered through a pad of celite. The celite pad was washed with 10 mL methanol. The filtrate was concentrated to give a dark brown residue was subjected to flash silica gel chromatography using 5% 2M NH3 in MeOH/CH2Cl2 to give an off-white solid (350 mg, 77.7%). 1H-NMR (DMSO-d6) δ: 6.81 (d, J=8.2 Hz, 1H), 6.46-6.41 (m, 2H), 4.84 (br s, 2H), 3.87 (t, J=7.1 Hz, 2H), 2.66 (t, J=6.5 Hz, 2H), 2.40-2.32 (m, 8H), 1.46-1.35 (m, 6H); MS (ESI): 274.2 (M+1, 100%).

Provenance & Evidence