Ammonia → HCID 43446597, compound

Participants

Reaction Steps

A solution of 1-(2-(diethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.72 mmol) in 10 mL methanol was added to Raney Nickel (slurry in H2O, 50 mg) in a round bottom flask. The suspension was treated with hydrazine hydrate (534 μL, 17.2 mmol) and heated at reflux for 10 minutes then filtered through a pad of celite. The celite pad was rinsed with 10 mL methanol. The filtrate was concentrated to give a dark brown residue which was subjected to flash silica gel chromatography using 5% 2M NH3 in MeOH/CH2Cl2 to give a colorless oil (365 mg, 81.2%). 1H-NMR (CDCl3) δ: 6.88 (d, J=8.4 Hz, 1H), 6.58 (d, J=2.7 Hz, 1H), 6.51 (dd, J=2.7, 9 Hz, 1H), 3.98 (t, J=7.8 Hz, 2H), 3.54 (br s, 2H), 2.78 (t, J=7.8 Hz, 2H), 2.66-2.55 (m, 8H), 1.04 (t, J=7.2 Hz, 6H). MS (ESI): 262.2 (M+1, 100%).

Provenance & Evidence