Abstract
5-Chloro- and 5-iodo-8-methylquinoline were obtained by chlorination or iodination of 8-methylquinoline with chlorine or iodine in concentrated sulfuric acid in the presence of silver sulfate. 5-Fluoro-8-methylquinoline was synthesized from 5-amino-8-methylquinoline. 5-Chloro-, 5-bromo-, and 5-fluoro-8-methylquinoline were converted to the corresponding 5-halo-8-(bromomethyl)quinolines by bromination with N-bromosuccinimide. Partial displacement of iodine by bromine to give a mixture of 5-bromo- and 5-iodo-8-(bromomethyl)quinoline occurs in the analogous bromination of 5-iodo-8-methylquinoline.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1373–1376, October, 1983.
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Tochilkin, A.I., Gracheva, I.N., Kovel'man, I.R. et al. Aromatic chlorination and iodination of 8-methylquinoline. Benzyl bromination of 5-halo-8-methylquinolines. Chem Heterocycl Compd 19, 1093–1096 (1983). https://doi.org/10.1007/BF00505763
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DOI: https://doi.org/10.1007/BF00505763