Conclusions
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1.
A study was made of the acid deuterium exchange of quinoline, quinaldine, and the 3-hydroxy- and 2-methyl-3-hydroxyquinolines at 145°. The protons of the benzene ring of the quinoline nucleus are the most reactive. The insertion of either a methyl or a hydroxy group into the pyridine ring increases the exchange rate of all of the protons of the benzene ring.
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2.
Exchange of the protons of the pyridine ring was observed only in 2-methyl-3-hydroxyquinoline, and it proceeded at a faster rate than in the 2-methyl- and 2,6-dimethyl-3-hydroxypyridines.
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Literature cited
V. P. Lezina, A. U. Stepanyants, L. D. Smirnov, N. A. Andronova, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, Ser. Khim., 1224 (1972).
V. Bressel, A. R. Katritzky, and J. R. Lea, J. Chem. Soc., B, 4 (1971).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2092–2094, September, 1972.
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Lezina, V.P., Stepanyants, A.U., Smirnov, L.D. et al. Study of acid deuterium exchange of quinoline, quinaldine, and 3-hydroxy-and 2-methyl-3-hydroxyquinolines. Russ Chem Bull 21, 2029–2031 (1972). https://doi.org/10.1007/BF00854634
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DOI: https://doi.org/10.1007/BF00854634