The conversion of benzoylacetanilides into 2- and 4-hydroxyquinolines

Relatively small proportions of polyphosphoric acid or anhydrous aluminum chloride convert benzoylacetanilides (II) to the corresponding 4-hydroxyquinolines (XII), while with excess of reagent the expected 2-hydroxyquinolines (IX) are furnished. A scheme to account for these results and for the action of acids on the anilide generally is discussed.