Aus Anthranilamid (I) wurde auf drei Wegen die Titelverbindung (IV) erhalten durch Umsetzen mit (a) Säurechlorid (II) zu (III) und nachfolgende Reduktion, (b) mit Isatinsäureanhydrid (V) und (c) mit dem Benzotriazinon (V).

Several synthetic routes to anthraniloylanthranilamide (6) are described; the problems involved in o-aminobenzoylation reactions are explored. Reduction of N-(o-nitrobenzoyl)anthranilamide by stannous chloride gave a low yield of 6, which was also obtained in low yield by reaction of isatoic anhydride with o-aminobenzamide. The possible use of O-(o-aminobenzoyl)hydroxylamines for o-aminobenzoylation was investigated but proved impractical. Diazotisation of 6 affords 3-(o-carbamoylphenyl)-1,2,3-benzotriazin-4(3H)-one (2), which undergoes base-catalysed cyclisation to the quinazolino[3,2-c]benzotriazine (4). The conversion 2 → 4 probably involves the isomeric quinazolino[1,2-c]benzotriazine (3), which could not be isolated.