Nitric Acid → 6, 7-Dichloro-3-nitro-4-hydroxy-1,2-dihydroquinolin-2-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1.25 g (5.43 mmol) of 5,6-dichloro-2,4-dihydroxyquinoline and 6,7-dichloro-2,4-dihydroxyquinoline in 8 mL of glacial acetic acid was added 1.5 mL of HNO3 (69-71%) and the mixture was heated at 90° C. for 2 h. The mixture was cooled to room temperature, filtered and washed with water, and dried to leave 280 mg (19%) of the title compound as a yellow solid, mp 235°-236° C. (decomposed). 1H NMR (CDCl3 +DMSO-d6), 7.362 (s, 1), 8.039 (s, 1), 11.369 (s, 1). MS, 274 (50, M+), 214 (100), 187 (18), 160 (20). High resolution MS, Calcd for C9H435Cl2N2O4 273.9544, found 273.9548.

Provenance & Evidence