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Gabriel synthesisThe Gabriel synthesis, named for the German chemist Siegmund Gabriel, is a chemical reaction that transforms primary alkyl halides into primary amines using potassium phthalimide.[1][2][3][4] Additional recommended knowledgeThe sodium or potassium salt of the product reacts with a primary alkyl halide to form an alkyl phthalic imide. The reaction fails with secondary alkyl halides. Upon workup by acidic hydrolysis the primary amine is liberated as the amine salt.[5] Alternatively the workup may be via the Ing-Manske procedure, involving reaction with aqueous or ethanolic hydrazine at reflux. This produces a precipitate of phthalhydrazide along with the primary amine. The first technique often produces bad yields or side products; separation of phtalhydrazide can be unpleasant. For these reasons, other methods for liberating the amine from the phthalimide exist.[6] References
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Gabriel_synthesis". A list of authors is available in Wikipedia. |