Synthetic Routes to Quinoline Derivatives:  Novel Syntheses of 3-Butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and 3-Butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline

The 3,4,8-trisubstituted quinoline derivatives 2-butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline were prepared using five novel synthetic strategies, each involving a different disconnection as a basis for the key step. One su...

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Published inOrganic process research & development Vol. 1; no. 3; pp. 185 - 197
Main Authors Atkins, Richard J, Breen, Gary F, Crawford, Lynne P, Grinter, Trevor J, Harris, Michael A, Hayes, Jerome F, Moores, Clive J, Saunders, Richard N, Share, Andrew C, Walsgrove, Timothy C, Wicks, Christopher
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.05.1997
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Summary:The 3,4,8-trisubstituted quinoline derivatives 2-butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and 3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline were prepared using five novel synthetic strategies, each involving a different disconnection as a basis for the key step. One such strategy led to the development of highly efficient processes for the large-scale preparations of both compounds and featured a facile cyclisation of an [(arylamino)methylene]malonate and an unusual Reformatsky reaction of a quinoline-3-carboxylate with tert-butyl 2-bromobutyrate in the presence of zinc.
ISSN:1083-6160
1520-586X
DOI:10.1021/op9700035