The Gabriel Synthesis of Primary Amines

Reaction of potassium phthalimide with halogenoalkanes and with a variety of other alkylating agents leads to the N-alkylphthalimide. N-Substituted phthalimides may be converted into the corresponding primary amine by hydrolysis or hydrazinolysis. The scope and limitations of these reactions, which together constitute the Gabriel Synthesis of primary amines, are reviewed.