N-Ethylaniline → HCID 54678936, compound

Participants

Reaction Steps

To an ice-cold solution of 1,2-dihydro-4-hydroxy-5-bromo-1-methyl-2-oxo-quinoline-3-carboxylic acid (9.6 g, 0.032 mol), triethylamine (15.5 ml, 0.11 mol) and N-ethylaniline (4.2 g, 0.035 mol) in 150 ml of dichloromethane was added dropwise during 0.5 hours a solution of thionyl chloride (3.0 ml, 0.042 mol) in 10 ml of dichloromethane. The stirring was continued at 4° C. for 24 hours. The solvents were evaporated. The residue was dissolved in ethyl acetate, filtered through celite and extracted with 2 M sodium hydroxide. The aqueous phase was washed with ethyl acetate and then acidified with hydrochloric acid to pH 5. On standing a crystalline precipitate was formed which was filtered off, washed with water and dried to give the title compound (8.5 g), yield 69%.

Provenance & Evidence