This invention relates to a novel chemical process for the synthesis of N'-benzyl-5- methylisoxazole-3-carbohydrazide (Isocarboxazid) which comprises reacting 5-methyl-3- isoxazole carboxylic acid ester with benzylhydrazine or a salt thereof in an aprotic organic solvent and in the presence of an organic base.
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Page/Page column 10; 11; 12
(2017/02/28)
Reductive alkylation of hydrazine derivatives with α-picoline-borane and its applications to the syntheses of useful compounds related to active pharmaceutical ingredients
An efficient method for the direct reductive alkylation of hydrazine derivatives with α-picoline-borane has been developed to synthesize a variety of N-alkylhydrazine derivatives. This method provided N,N-dialkylhydrazine derivatives and N-monoalkylhydrazine derivatives upon fine-tuning of the substrates and the reagent equivalency in a one-pot manner. The method was applied to the synthesis of active pharmaceutical ingredients of therapeutic drugs such as isocarboxazid.
The Boulton-Katritzky rearrangement of isocarboxazid
(Chemical Equation Presented) Isocarboxazid rearranges on heating to 5-acetonyl-2-benzyl-4-hydroxy-1,2,3-triazole in DMF at 150°C, in the ionic liquid, [bmin]HSO4- at 100°C or as a melt at 105°C. This is the first reported example of the Boulton-Katritzky rearrangement of an acyl hydrazide.
Van Arnum, Susan D.,Niemczykapi, Henry J.
experimental part
p. 909 - 913
(2010/01/11)
Monoamine oxidase inhibitors. I. 1-Alkyl and 1-aralkyl-2-(picolinoyl and 5-methyl-3-isoxazolyl-carbonyl)hydrazines.