Organic Synthesis

Phthalimide is treated with a KOH/H2O, then mixed with an alkyl or aryl halide. Then is treated with NaOH to hydrolyse the phthalimide condensation product to the 1° amine and 2-(Carboxycarbonyl)benzoic acid. This has a strong advantage over the standard alkyl condensation with ammonia or an amine in that it is self-limiting to a primary amine, given the phthalimide is no longer a nucleophile after the condensation.