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2-(2-Aminophenyl)-acetaldehyde Dimethyl Acetal: A Novel Reagent for the Protection of Carboxylic Acids.

✍ Scribed by Eri Arai; Hidetoshi Tokuyama; Martin S Linsell; Tohru Fukuyama

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 439 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10491-9

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✦ Synopsis

The synthesis and use of 2-(2-aminophenyl)-acetaldehydedimethyl acetal 1 are described, The amides 2, derived from this amine and carboxylicacids, are stable under basic conditions and thus can be regardedas the protectedcarboxylicacids. The correspondingcarboxylicacids are regeneratedby conversion of 2 into indolybunides3 by treatment with CSA and subsequent hydrolysis with LiOOH or NaOH. In addition,3 can be easily convertedto esters, amides,and aldehydes.

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