Potassium Carbonate → 1-(2-(dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Steps

6-Nitro-3,4-dihydroquinolin-2(1H)-one (5 g, 25.61 mmol) and 2-chloro-N,N-dimethylethanamine hydrochloride (7.38 g, 51.23 mmol) were weighed into a round bottom flask and stirred in DMF (50 mL). To this solution/suspension was added potassium carbonate (21.59 g, 156.2 mmol). The resulting suspension was stirred overnight at room temperature. The reaction mixture was then poured into ice water (150 mL) and extracted with ethyl acetate (2×100 mL). The combined organics were washed with water (1×) and brine (1×). The organic phase was dried over sodium sulfate, filtered and concentrated. The resulting residue was chromatographed in 0-20% (2M NH3 in MeOH) in 1:1 dichloromethane and ethyl acetate, giving a yellow solid. Yield: 5.8 g, 84%. 1H NMR (CDCl3) δ 8.14 (dd, 1H, J=9.0, 3.0 Hz) 8.06 (d, 1H, J=3.0 Hz), 7.16 (d, 1H, J=9.0 Hz), 4.08 (t, 1H, J=7.5 Hz), 3.00 (t, 1H, J=7.5 Hz), 2.70 (t, 1H, J=7.5 Hz); 2.51 (t, 1H, J=7.5 Hz), 2.31 (s, 6H).

Provenance & Evidence