Ing-Manske modification

A commonly used modification of the Gabriel synthesis is the Ing-Manske procedure.10 Instead of removal of the phthaloyl group with aqueous base or acid, the Ing-Manske modification utilizes hydrazinolysis. It has been used in the synthesis of optically active a-amino acids 17, as illustrated by Guifa and Lingchong.11... 

As well as amines, the Ing-Manske modification has also been used to synthesise O-substituted hydroxy lam ines, for example, 20.12 The hydroxyamines thus obtained were subsequently condensed with steroids to form O-alkyloximes. 

B. Gabriel Condensation and Ing-Manske Modification 13-S. Preparation of a, Diaminoadipic Add... 

For the sake of applicability, the preparation of a,(5-diaminoadipic acid using the Ing-Manske modification is given here, although the same reference indicates that, at least in this case, the Gabriel condensation and hydrolysis affords a higher yield. 

Gabriel condensation, 124-126 Ing-Manske modification, 124-126 Gattermann condensation, 50 Goldberg reaction, 93 Grignard coupling, 14-15,17 Grignatd method, 54-56 Grignard reaction, 31,50, 59,94,176,187, 246-248... 

Another method for the preparation of primary amines involves the alkylation of potassium phthalimide according to procedures of Gabriel to give A-alkylphthalimides, which, on hydrolysis, afford the primary amine and phthalic acid. Since the hydrolysis is sometimes difficult, Ing and Manske [18] developed a modification in which the decomposition of the A-alkylphthalimide is carried out in the presence... 

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