Anthranilic Acid → Anthranil

Participants

Reaction Steps

reacting a compound of the formula ##STR85## wherein L is a leaving group, with a hydroxylamine hydrochloride to form an isonitrosoacetanilide compound of the formula ##STR86## (2) treating the isonitrosoacetanilide compound of step (1) with acid, followed by addition of ice and purification with alcohol, to obtain an isatin compound of the formula ##STR87## (3) reacting the isatin compound of step (2) with an aqueous basic peroxide to form an anthranilic acid compound of the formula ##STR88## (4) reacting the anthranilic acid compound of step (3) with acetic anhydride to form an acetylanthranil compound of the formula ##STR89## (5) treating the acetylanthranil compound of step (4) with alcohol, followed by acid, to obtain a compound of the formula ##STR90## and (6) reacting the product of step (5) with chloroformamidine hydrochloride to obtain a quinazoline compound of the formula ##STR91##

Provenance & Evidence