Phthalimide on treatment with ethanolic potassium hydroxide forms
potassium salt of phthalimide which on heating with alkyl halide
followed by alkaline hydrolysis produces the corresponding primary
amine Aromatic primary amines cannot be prepared by this method
because aryl halides do not undergo nucleophilic substitution with
the anion formed by phthalimide 6 Hoffmann bromamide degradation reaction
Hoffmann developed a method for preparation of primary amines by
treating an amide with bromine in an aqueous or ethanolic solution
of sodium hydroxide