Sodium Iodide → 1-(2-morpholinoethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

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Reaction Steps

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (1.00 g, 5.20 mmol), 4-(2-chloroethyl)morpholine hydrochloride (1.94 g, 10.40 mmol), sodium iodide (390 mg, 2.61 mmol) and potassium carbonate (4.32 g, 31.3 mmol) in DMF (5 mL) was stirred at room temperature for 60 hours. The mixture was transferred to a separatory funnel, diluted with water (45 mL) then extracted with ethyl acetate (3×35 mL). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was subject to flash chromatography on silica gel using 2.5% 2M NH3 methanol/CH2Cl2, which resulted in a yellow solid, compound 2 (0.9211 g, 58%).

Provenance & Evidence