Potassium Iodide → HCID 53392258, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (5.22 g, 19.43 mmol), potassium iodide (3.22 g, 19.43 mmol) and potassium carbonate (16.11 g, 117 mmol) in acetonitrile (100 ml) was added dimethylamine hydrochloride (6.34 g, 78 mmol). The resulting mixture was stirred overnight at 50° C. The mixture was then cooled to room temperature, diluted with water and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in dichloromethane as the eluent. 1H NMR (DMSO-d6) δ 8.14-8.10 (m, 2H), 7.37 (d, J=9.6 Hz, 1H), 3.94 (t, J=7.5 Hz, 2H), 3.00 (t, J=7.5 Hz, 2H), 2.62 (t, J=7.5 Hz, 1H), 2.27 (t, J=7 Hz, 2H), 2.13 (s, 6H), 1.66 (quint, J=7.5 Hz, 1H). ESI-MS (m/z, %) 278 (MH+, 100).

Provenance & Evidence