Abstract
Pyridinecarboxylic acids undergo esterification on refluxing with alcohols in the presence of cation-exchange resins. In the case of pyridine-2,6-dicarboxylic acid, in which the basicity of the nitrogen atom is reduced, esterification products are obtained in high yields. In the case of pyridinecarboxylic acids, in which the pyridine nitrogen atom displays considerable basicity, the cations of the acids are tied up by the cation-exchange resin, and the yields of preparatively isolable esters do not exceed 60%.
Similar content being viewed by others
Literature cited
N. G. Polyanskii, Catalysis by Ion-Exchange Resins [in Russian], Moscow (1973), p. 213.
M. V. Rubtsov, E. S. Nikit-skaya, and V. S. Usovskaya, Zh. Obshch. Khim., 26, 130 (1956).
A. D. Lourie, J. Med. Chem., 9, 311 (1966).
H. Meyer, Monatsh., 24, 195 (1903).
R. Turnau, Monatsh., 29, 845 (1908).
A. Lupu and M. Opris, Rev. Chim., 10, 607 (1959).
E. Fujita, K. Fuji, K. Bessho, and S. Nakamura, Chem. Pharm. Bull., 18, 2393 (1970).
E. Swistak and P. Mastagli, Compt. Rend., 239, 709 (1954).
L. N. Yakhontov and M. D. Mashkovskii, Khim.-Farmats. Zh. (1976, in press).
R. A. Barnes and H. M. Fales, J. Amer. Chem. Soc., 75, 3830 (1953).
V. Boekelheide and W. J. Linn, J. Amer. Chem. Soc., 76, 1286 (1954).
C. Engler, Ber., 27, No. 2, 1786 (1894).
R. Graf and F. Zettle, J. Prakt. Chem., 147, 188 (1936).
H. Adkins, L. F. Kuick, M. Farlow, and B. Wojcik, J. Amer. Chem. Soc., 56, 2425 (1934).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 233–237, February, 1976.
Rights and permissions
About this article
Cite this article
Levkoeva, E.I., Mastafanova, L.I., Krasnokut-skaya, D.M. et al. Esterification of pyridinecarboxylic acids in the presence of cation-exchange resins. Chem Heterocycl Compd 12, 201–204 (1976). https://doi.org/10.1007/BF00523971
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00523971