Ammonia → 6-amino-3-(3-(dimethylamino)propyl)-1-(4-methoxybenzyl)-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Steps

A solution of 3-(3-(dimethylamino)propyl)-1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (115 mg, 0.29 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 (90 μL, 2.90 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 yellow residue which was subjected to flash silica gel chromatography using 5% 2M NH3 in MeOH/CH2Cl2 to give a yellow semi-solid (77 mg, 72.3%). 1H-NMR (CDCl3) δ: 7.13-7.10 (m, 2H), 6.83-6.80 (m, 2H), 6.69 (d, J=8.4 Hz, 1H), 6.50 (d, J=2.4 Hz, 1H), 6.42 (dd, J=2.4, 8.4 Hz, 1H), 5.05 (dd, J=15.6, 29.1 Hz, 2H), 3.76 (s, 3H), 3.48 (br s, 2H), 3.01-2.91 (m, 1H), 2.70-2.58 (m, 2H), 2.28 (t, J=7.2 Hz, 2H), 2.21 (s, 6H), 1.88-1.42 (m, 4H).

Provenance & Evidence