4-Nitrophthalimide → 1,2-Benzenedicarboxamide, 4-nitro-

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Commercial 4-nitrophthalimide (500 g; 2.60 moles; mp 196°-200° C) is added quickly to a stirred solution of 15.6 N ammonium hydroxide (3500 ml). With continued stirring, external heating (water bath, 45° C) is applied until frothing ceases (1 hour). The resulting precipitate is collected, washed with ice water (2 × 400ml) then recrystallized with acetone (2 × 400 ml) and dried to yield 440 g of I as pale yellow crystals; yield, 81%, mp 200°-202° C; lit (6) mp 200° C.

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