8-Nitroquinolin-2(1H)-one

4225-86-9

7461-12-3

General procedure for the synthesis of 8-nitroquinolin-2(1H)-ones from 2-chloro-8-nitroquinoline: 2-chloro-8-nitroquinoline (1 equiv.) was dissolved in acetonitrile (25 mL) and 70% perchloric acid solution (25 mL) was added. The reaction mixture was stirred at 100°C overnight. Upon completion of the reaction, the mixture was poured into ice water and neutralized to neutral with KOH solution. The organic layer was extracted twice with dichloromethane and combined. The organic layer was washed with water and then dried with anhydrous MgSO4. After drying, the solvent was removed by vacuum evaporation to give the crude product. Purification by silica gel column chromatography using a suitable eluent and recrystallization if necessary gave the target compound 8-nitroquinolin-2(1H)-one. Isolation of 4-methyl-8-nitroquinolin-2(1H)-one 7 (C10H8N2O3) and recrystallization resulted in a yellow solid in acetonitrile in 92% yield (11 mmol, 2.2 g).