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40.1.1.5.4.3.4 Method 4: The Gabriel Synthesis and Related Reactions of Carboxylic Acid Derivatives

DOI: 10.1055/sos-SD-040-00344

Lawrence, S. A.Science of Synthesis, (200940531.

The Gabriel synthesis of amines involves the reaction of a metal phthalimide, usually potassium phthalimide (72), with an organic halide and subsequent cleavage of the alkyl phthalimide 73 to release a primary amine 74 (Scheme 53; see also HoubenWeyl, Vol. 11/1, pp 7996).[‌151‌‌156‌] Cleavage of the N-alkylated phthalimide can be accomplished by acid- or base-catalyzed hydrolysis or by the IngManske modification, which uses hydrazine hydrate in methanol or ethanol.[‌153‌]

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