4-Bromoaniline → 6-Bromo-4-hydroxyquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

According to the general method described in Synth. Commun. 2010, 40, 732, a mixture of 4-bromoaniline (10.0 g, 58.1 mmol) and 2,2-dimethyl-1,3-dioxan-4,6-dione (8.40 g, 58.1 mmol) was heated at 80° C. for 1 hour and cooled to room temperature to receive 3-((4-bromophenyl)amino)-3-oxopropanoic acid as a solid. A stream of nitrogen gas was passed over the solid product to remove liquid acetone formed as a by-product. To this solid was added Eaton's reagent (40 mL) and the mixture was heated at 70° C. for 12 hours and then cooled to room temperature. To the resulting mixture was added water and stirred vigorously to receive a suspension which was filtered. The solid residue was washed with water and dried in air to yield the title compound.

Provenance & Evidence