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Please login to access the full content or check if you have access via 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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Me ee eeeeeeeeeee ee eeeee eeeeeeeeeeee, eeeeee eeeeeeeeeeeee (88) eeeeee eeee eeeee eeeeeee ee eeee ee eeeeeeeeeeeeeeee, eeeee ee eeee eeeeeeeeee ee eee eeeee 88 (Meeeee 88). Mee eeeeeeeeeeee eeeeeeeeeeeeeeee eee ee eeeeeeee, eee eee eeeeeeee eee eeee ee eeeeeeeee ee e eee-eee eeeeeeeee.[‌888‌]

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Meeeeeeeeee 88

M8M Meeee (%) ee 88 Meeeeeeee Meeeeeee Meeeeee Meeeee (%) ee 88 Mee
Me(MM8)8Me 88 e.e. e.e. [‌888‌]
Me(MM8)8Me 88 M 88 [‌888‌]
Me(MM8)8M 88 M 88 [‌888‌]
MeMe 88 M 88 [‌888‌]
MeMM=MMMM8Me 88 M 88 [‌888‌]
MeM8MMM8Me 88 M 88 [‌888‌]
MeM8MMM8Me 88 M 88 [‌888‌]
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