Sodium Iodide → HCID 53392179, compound

Participants

Reaction Steps

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (2.0 g, 10.4 mmol), 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (3.83 g, 20.8 mmol), sodium iodide (779 mg, 5.20 mmol) and potassium carbonate (8.63 g, 62.4 mmol) in dimethylformamide (15 mL) was stirred at room temperature overnight. After this time, the mixture was diluted with water (15 mL) then extracted with ethyl acetate (3×75 mL). 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 an orange oil which solidified upon drying under reduced pressure (2.32 g, 73.7%). 1H-NMR (CDCl3) δ: 8.13 (dd, J=2.7, 9 Hz, 1H), 8.05 (d, J=2.4 Hz, 1H), 7.11 (d, J=9.0 Hz, 1H), 4.15-4.05 (m, 1H), 3.97-3.87 (m, 1H), 3.05-3.01 (m, 4H), 2.72-2.70 (m, 2H), 2.28 (s, 3H), 2.17-1.60 (m, 7H).

Provenance & Evidence