Gabriel synthesis of primary amine

The simplicity of the two-phase modification of the Gabriel synthesis of primary amines, via the N-alkylation of potassium phthalimide, makes the procedure considerably more convenient than the traditional method, which normally requires the use of anhydrous dipolar aprolic solvents. The reaction can be conducted under solid liquid conditions using potassium hydroxide in toluene [25], or with preformed potassium phthalimide [26, 27] (cf ref. 28). As is normal for acylation reactions, relatively mild conditions are required for the preparation of the A-ethoxycarbonyl derivative [29], whereas a reaction temperature of 100°C is generally used for N-alkylation (Table 5.16). The reaction time for the soliddiquid two-phase system can be reduced dramatically with retention of the high yields, when the reaction mixture is subjected to microwave irradiation [30]. 

Saccharin in the Gabriel synthesis of primary amines 91ACR285. 

Silacyclopentane derivatives in Peterson olefination 91SL764. 2,2,6,6-Tetramethyl-2,6-disilapiperidine in the Gabriel synthesis of primary amines 91ACR285. 

Alkylation of phthalLmide is the first step in the Gabriel synthesis of primary amines. The scope of this alkylation is discussed in method 452 because the phthalimides are often hydrolyzed directly, without purification, to primary amines. 

Khan, M. N. Suggested Improvement in the Ing-Manske Procedure and Gabriel Synthesis of Primary Amines Kinetic Study on Alkaline Hydrolysis of N-Phthaloylglycine and Acid Hydrolysis of N-(o-Carboxybenzoyl)glycine in Aqueous Organic Solvents. J. Org. Chem. 1996,... 

Synthesis of primary amines. Hendrickson and co-workers have prepared two derivatives, (1) and (2), of N-benzyltriflamide that can be used for a one-flask Gabriel synthesis of primary amines. These reagents undergo alkylation... 

Gabriel synthesis of primary amines. More recently, phthalimide has been used in a... 

Gabriel synthesis of primary amines reaction of a primary alkyl halide with potassium phthalimide (16.18). 

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