Acetic Acid → 1-Ethyl-4-hydroxyquinolin-2(1H)-one

Participants

Reaction Steps

A solution of N-ethyl anthranilic acid (12.0g; 0.073 mole) in acetic acid (37 ml) and acetic anhydride (37ml) was refluxed for 4 hrs. The red solution was cooled, poured onto crushed ice and made alkaline with aqueous sodium hydroxide. After filtering the yellow filtrate was neutralised with concentrated hydrochloric acid (pH 5) and the yellow solid filtered and washed with water. Recrystallisation from acetic acid in the presence of charcoal gave the title compound as an orange solid, m.p. 273°-275° C. (Found: C, 69.85; H, 6.04; N, 7.29; C11H11NO2 requires: C, 69.83; H, 5.86; N, 7.40%).

Provenance & Evidence