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

Participants

Reaction Steps

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 2.60 mmol), (N,N-dimethylamino)ethyl chloride hydrochloride (412 mg, 2.86 mmol) and potassium carbonate (1.07 g, 7.74 mmol) in 8 mL DMF was stirred at room temperature for 48 hours. Additional (N,N-dimethylamino)ethyl chloride hydrochloride (187 mg, 1.30 mmol) and potassium carbonate (359 mg, 2.60 mmol). Reaction was stirred for an additional 16 hours. After this time, the reaction was transferred to a separatory funnel and diluted with cold water and ethyl acetate. The aqueous was extracted twice more with ethyl acetate and the combined organic fractions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a yellow solid. Yield: 370 mg (54%). 1H NMR (CDCl3) δ: 8.15 (dd, J=2.7, 9.0 Hz, 1H), 8.06 (d, J=2.7 Hz, 1H), 7.17 (d, J=9 Hz, 1H), 4.09 (t, J=7.2 Hz, 2H), 3.00 (t, J=6.6 Hz, 2H), 2.71 (t, J=7.5 Hz, 2H), 2.52 (t, J=7.5 Hz, 2H), 2.32 (s, 6H). MS (ESI): 264.1 (M+1).

Provenance & Evidence