The chemistry of 2H-3,1-benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 19. Direct formation of 2-aminobenzyl alcohols from the reduction of N-substituted isatoic anhydrides

Isatoic anhydrides 1 are easily reduced with sodium borohydride to o-(substituted-amino)benzyl alcohols 3 in good yield. Sequential reduction of N-(2-nitrobenzyl)isatoic anhydride ( 5 ) with sodium borohydride followed by catalytic hydrogenation of the nitro group affords the naturally occurring 2-(2′-aminobenzylamino)-benzyl alcohol ( 4 ) in 72% yield.