Nitric Acid → 4-Chloro-8-nitroquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloroquinoline (1.0 g, 6.13 mmol) in conc. H2SO4 (4.5 mL) was drop wise added conc. HNO3 (1.8 mL) at 0° C. and the reaction mixture was stirred at 0-15° C. for 3 h. Then the reaction mixture was quenched by addition of aq. NH4OH at 0° C. and the pH of the reaction mixture was adjusted to 8. The solid precipitate was filtered and the filter cake was further purified by column chromatography to afford 900 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.98 (d, J=5.1 Hz, 1H), 8.50-8.47 (d, J=9.0 Hz, 1H), 8.41 (d, J=7.8 Hz, 1H), 8.02-7.99 (d, J=4.8 Hz, 1H), 7.96-7.90 (t, J=7.8 Hz, 1H).

Provenance & Evidence