Hydrochloric Acid → 2-(3-Bromophenyl)-6-fluoro-3-methyl-4-quinolinecarboxylic acid

Participants

Reaction Steps

Potassium hydroxide (19.98 g, 356 mmol) was added to a suspension of 5-fluoro-1H-indole-2,3-dione (10 g, 59.4 mmol) in ethanol (96 mL). 1-(3-Bromophenyl)-1-propanone (13.91 g, 65.3 mmol) was added and the mixture was heated to reflux for 1 h. The reaction mixture was cooled to room temperature and acidified to pH 3 with concentrated HCl. The solid was collected by filtration, washed with water, and dried to afford 2-(3-bromophenyl)-6-fluoro-3-methyl-4-quinolinecarboxylic acid (20.9 g, 98% yield). This material was used without further purification. MS (m/z) 360.0 (M+H+).

Provenance & Evidence