Potassium Iodide → HCID 59807141, compound

Participants

Reaction Steps

To a stirred mixture of 1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.861 mmol) and potassium carbonate (1286 mg, 9.30 mmol) in acetonitrile (5 ml) was added 2-(methylamino)ethanol (0.447 ml, 5.58 mmol). The resulting mixture was stirred overnight at room temperature under argon. The reaction mixture was then diluted with water and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed on silica gel using ethyl acetate as eluent, followed by 10% (2M NH3 in methanol) in dichloromethane. A large amount of starting material was recovered and resubjected to the reaction conditions, using potassium iodide, and heating overnight at 80° C. followed by workup and repurification.

Provenance & Evidence