The Gabriel phthalimide synthesis is a method used to prepare primary aliphatic and aromatic amines. The process begins with phthalimide being treated with ethanolic potassium hydroxide (KOH), forming the potassium salt of phthalimide. This salt is then heated with an alkyl halide (RX), and subsequent treatment with either alkaline hydrolysis or hydrazinolysis (using hydrazine, $ \mathrm{H}_2\mathrm{N} \cdot \mathrm{NH}_2 $) yields the corresponding primary amine. However, this method cannot be used to synthesize primary aromatic amines that have electron-withdrawing groups (EWGs) at the ortho- and para-positions, such as the nitro group ($ -\mathrm{NO}_2 $). This limitation arises because aryl halides (ArX) do not undergo nucleophilic substitution ($\mathrm{S}_{\mathrm{N}}$) reactions with the anion formed by phthalimide.