Summary
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1.
A study was made of the comparative reactivity of the ortho- and para-positions of 3-hydroxypyridine and 6-methyl-3-hydroxypyridine in the aminomethylation reaction.
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In contrast to phenol,β-pyridinol forms only the 2,6-bis-substituted products, while 6-in ethyl-3-hydroxypyridine forms only the 2-monosubstituted compounds. Substitution in the 4 position was not observed in either case.
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Literature cited
K. M. Dyumaev, L. D. Smirnov, and V. F. Bystrov, Izv. AN SSSR, Otd. khim. nauk,1962, 883.
L. D. Smirnov, V. P. Lezina, V. F. Bystrov, and K. M. Dyumaev, Izv. AN SSSR, Ser. khim., (in press).
A. Stempel and E. C. Buzzi, J. Amer. Chem. Soc.,71, 2969 (1949).
T. Urbanski, J. Chem. Soc.,1946, 1104.
R. F. Brown and S. J. Miller, J. Org. Chem.,11, 388 (1946).
L D. Smirnov, V. P. Lezina, V. F. Bystrov, and K. M. Dyumaev, Izv. AN SSSR, Ser. khim.,1963, 752.
H. Hellman and G. Opitz,α-Aminoalkylierung (1960), p. 140.
A. F. Holleman, Recueil trav. chim.,22, 263 (1903).
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The authors wish to thank N. M. Emanuel for his constant interest in the work.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 198–200, January, 1965
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Smirnov, L.D., Lezina, V.P., Bystrov, V.F. et al. Study of the comparative reactivity of the ortho- and para-positions of 3-hydroxypyridine and 6-methyl-3-hydroxypyridine during aminomethylation. Russ Chem Bull 14, 188–190 (1965). https://doi.org/10.1007/BF00854892
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DOI: https://doi.org/10.1007/BF00854892