Gabriel phthalimide synthesis: The reaction of phthalimide with ethanolic KOH gives potassium salt of phthalimide. It is then heated with alkyl halide to form N-alkyl phthalimide. Alkaline hydrolysis (or treatment with hydrazine) gives a primary amine. Secondary or tertiary amines are not obtained as over alkylation is avoided. Aromatic primary amines cannot be prepared as aryl halides do not undergo nucleophilic substitution with anion formed by phthalimide.