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

Participants

Reaction Conditions

Reaction Steps

To a solution of hydrocarbostyril (7.8 g, 0.53 mol) in conc. H2SO4 (200 mL) was slowly added H2O (50 mL) at −10° C. Conc. HNO3 (70%, 4.0 mL) was added dropwise at −10° C. The yellow solution was stirred at −10° C. for 10 min and then carefully quenched with ice H2O (500 mL). The precipitated yellow solid was filtered, washed with H2O and dried under vacuum to obtain 6-nitro-3,4-dihydroquinolin-2(1H)-one (7.9 g, 78% yield). 1H NMR (400 Mhz, CDCl3): δ 9.28 (s, 1H), 8.12 (m, 2H), 6.95 (d, J=9.2 Hz, 1H), 3.12 (t, J=7.2 Hz, 2H), 2.75 (d, J=7.2 Hz, 2H).

Provenance & Evidence