Nitric Acid → 6-Nitro-3,4-dihydroquinolin-2(1H)-one

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Reaction Steps

To a solution of 3,4-dihydroquinolin-2-(1H)-one (1.50 g) in 78% sulfuric acid (300 mL) at RT, a mixture of 69% nitric acid (0.84 mL) in 78% sulfuric acid (60 mL) was added. The reacting mixture was stirred at RT for 15 min, poured into ice-water, and extracted with methylene chloride (3×200 mL). The organic extracts were combined, washed with brine (4×), dried over anhydrous magnesium sulfate, filtered and concentrated onto silica gel. The residue was loaded onto a column of silica gel, and eluted with 3% methanol in chloroform. Collection and concentration of appropriate fractions provided the nitroquinolinone 11-2.

Provenance & Evidence