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Sequence of replacement of hydrogen in 2,6-dimethylpyridine by lithium or halogen

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown that, according to the results of chromatographic mass spectrometry, the reaction of 2,6-dimethylpyridine with phenyllithium leads only to the monolithium derivative. The chlorination and bromination of 2,6-dimethylpyridine with various reagents were studied systematically. A method for the conversion of 2,6-bis(chloromethyl)pyridine to 2,6-bis(hydroxymethyl)pyridine is given.

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Literature cited

  1. Y. I. Yong and Y. P. Wibaut, Rec. Trav. Chim., 70, 962 (1951).

    Google Scholar 

  2. E. D. Bergman and S. Pinchas, J. Org. Chem., 15, 1184 (1950).

    Google Scholar 

  3. R. A. Barnes and H. M. Fales, J. Am. Chem. Soc., 75, 3830 (1953).

    Google Scholar 

  4. Hasegawa, Pharm. Bull. Jpn., 47, 293 (1953).

    Google Scholar 

  5. W. Offermann and F. Vögtle, Synthesis, 272 (1977).

  6. French Patent No. 1394362 (1965); Chem. Abstr., 63, 8326 (1965).

  7. T. Hattory, Japan Kokai, 74127977 (1974); Chem. Abstr., 84, 121665 (1976).

    Google Scholar 

  8. E. T. McBee, H. B. Hass, and E. M. Hodnett, Ind. Eng. Chem., 39, 389 (1947).

    Google Scholar 

  9. R. Graf and H. Zete, J. Prakt. Chem., 147, 188 (1935).

    Google Scholar 

  10. L. Does and H. J. Hertog, Rec. Trav. Chim., 91, 1403 (1972).

    Google Scholar 

  11. J. Abblard, C. Decoret, and L. Cronenberger, Bull. Soc. Chim. Fr., 2466 (1972).

  12. T. Kato, H. Hayashi, and T. Anzai, Yakugaku Zasshi, 87, 387 (1967).

    Google Scholar 

  13. W. Baker, K. M. Buggle, and McOmie, J. Chem. Soc., 3594 (1958).

  14. W. Mathes and H. Shülz, Angew. Chem., 75, 235 (1963).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 105–110, January, 1980.

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Karpman, Y.S., Azimov, V.A., Anisimova, O.S. et al. Sequence of replacement of hydrogen in 2,6-dimethylpyridine by lithium or halogen. Chem Heterocycl Compd 16, 89–93 (1980). https://doi.org/10.1007/BF00475401

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  • DOI: https://doi.org/10.1007/BF00475401

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