Potassium Iodide → HCID 59807103, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (100 mg, 0.359 mmol), morpholine (313 uL, 3.59 mmol), potassium iodide (596 mg, 3.59 mmol) and potassium carbonate (496 mg, 3.59 mmol) were weighed into an argon purged vial fitted with a magnetic stirbar. Anhydrous acetonitrile (4 mL) was added, and the yellow suspension stirred in a heating block at a temperature of 65° C. for 18 hours. As starting material remained, the reaction was stirred at this temperature for an additional 3 days. After cooling to room temperature, the reaction was diluted with water (10 mL) and dichloromethane (15 mL) and transferred to a separatory funnel. The organic layer was collected, and the aqueous layer extracted twice more with dichloromethane (2×10 mL). The combined organics were washed with brine (15 mL) and dried over sodium sulphate. The solution was decanted and concentrated to afford a yellow oil. The product was purified using flash chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5-5:95-97.5) to afford a yellow oil. Yield: 88 mg yellow oil (77%). 1H-NMR (CDCl3) δ: 8.13 (dd, J=2.7, 9 Hz, 1H), 8.07 (d, J=2.4 Hz, 1H), 7.21 (d, J=9.0 Hz, 1H), 4.04 (t, J=7.5 Hz, 2H), 3.72 (t, J=4.5 Hz, 4H), 3.01 (t, J=7.2 Hz, 2H), 2.73-2.68 (m, 2H), 2.46-2.39 (m, 6H), 1.88-1.79 (m, 2H). MS (EI): 319 (M+).

Provenance & Evidence