N-Phenylanthranilic Acid → 4-Hydroxy-1-phenyl-1,2-dihydroquinolin-2-one

Participants

Reaction Steps

A solution of N-phenyl anthranilic acid (30.1g.; 0.146 mole) and acetic anhydride (74 ml.) in glacial acetic acid (74 ml.) was refluxed for 4 hrs. The resulting red solution was cooled, poured onto crushed ice-water (600 ml) and brought to pH 9 with dilute sodium hydroxide solution. After filtration the clear liquid was taken to pH 5 with hydrochloric acid and the white solid filtered off and dried, m.p. (AcOH) 298°-300°C. (Found: C, 75.40; H, 4.58; N, 5.70; C15H11NO2 requires; C, 75.94; H, 4.67; N, 5.90%).

Provenance & Evidence