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Reactions of 6-methyl- and 4,6-dimethyl-2-arylaminonicotinonitriles with acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A substituted nicotininc acid is formed when 6-methyl-2-anilinonicotinonitrile is refluxed with concentrated hydrochloric acid, whereas 4,6-dimethyl-2-anilinonicotinonitrile is not hydrolyzed under these and more severe conditions because of steric hindrance. Both of these nitriles undergo cyclization to 10-aminobenzo-[b]-l,8-naphthyridine derivatives under the influence of concentrated sulfuric acid. When 6-methyl-2-arylaminonicotinonitriles are heated in polyphosphoric acid (PPA), they are converted to 2-arylaminonicotinic acid amides and, in part, to benzo[b]-l,8-naphthyrid-10-one derivatives, while 4,6-dimethyl-2-arylaminonicotinonitriles are converted primarily to 10-aminobenzo[b]-l,8-naphthyridines.

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Authors and Affiliations

  1. Perm Pharmaceutical Institute, 614600, Perm

    N. I. Shramm & M. E. Konshin

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  1. N. I. Shramm
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  2. M. E. Konshin
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 674–678, May, 1982.

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Shramm, N.I., Konshin, M.E. Reactions of 6-methyl- and 4,6-dimethyl-2-arylaminonicotinonitriles with acids. Chem Heterocycl Compd 18, 511–515 (1982). https://doi.org/10.1007/BF00526089

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  • DOI: https://doi.org/10.1007/BF00526089

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