Hydrogenation of benzo[c]quinolizinium chloride (2) saturates first ring A and then ring B. Oxidation of compound (2) destroys ring A, affording quinoline-2-carboxylic acid; nucleophilic attack by sodium hydroxide and hydroxylamine yields 3-hydroxy-4-(2-quinolyl)butyronitrile (14). Nitration of compound (2) occurs at position 10.
A. Fozard, L. S. Davies, C. K. Bradsher and P. M. Gross, J. Chem. Soc. C, 1971, 3650 DOI: 10.1039/J39710003650
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