Abstract: | The acid catalyzed reaction of anthranilamide with benzoin was studied under two conditions. Condensation at 150° gave known J plus unexpected quinazolinone H. In refluxing benzene (azeolropic water removal), the reactants yielded imine III. The acid catalyzed and uncatalyzed 150° reaction of III was examined by both ir and tlc. Both benzoic acid and II were formed in each case. Triethyl ortholormate with I gave quinazolinone IV while this ester with III formed II, benzaldehyde and benzoic acid. |