Gabriel synthesis

The Gabriel synthesis is an organic reaction used to convert an alkyl halide to a primary amine using phthalimide with base and followed by hydrazine. The reaction begins with the deprotonation of the phthalimide which then attacks the alkyl halide in an S_N2 fashion to give an N-alkylphthalimide intermediate. The intermediate is then cleaved by hydrazine in a series of steps that end with the liberation of the final primary amine product and phthalhydrazide by-product.^[1]