Morpholine → HCID 59807103, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension 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 (10 ml) was added morpholine (0.814 ml, 9.30 mmol) via a syringe. The resulting suspension was then stirred overnight at 75° C. in a sealed tube. The reaction 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 in ethyl acetate, followed by 5% (2M NH3 in methanol) in dichloromethane, giving the desired 1-(3-morpholinopropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (560 mg, 1.754 mmol, 94% yield). 1H NMR (DMSO-d6) δ 8.14-8.10 (m, 2H), 7.40 (d, J=9 Hz, 1H), 3.95 (t, J=7.4 Hz, 2H), 3.58-3.54 (m, 4H), 3.03-2.97 (m, 2H), 2.64-2.59 (m, 2H), 2.33-2.28 (m, 6H), 1.74-1.64 (m, 2H).

Provenance & Evidence