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Alkylation of 4-picolinium salts under phase transfer conditions

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Alkylation of 1-ethyl-4-methylpyridinium bromide by allyl, benzyl and propargyl chlorides has been effected under conditions of phase transfer catalysis in a solid phase-liquid system (K2CO3-CHCl3). Using the example of alkylation by allyl chloride, the effect of the concentration and the nature of the catalyst, the concentration of the base, and the temperature on the yield of mono-, di-, and trisubstituted products has been studied. The reactivity of the alkyl chlorides increases in the order allyl < benzyl < propargyl. When the reaction is carried out in a liquid—liquid system (25% aqueous NaOH-CHCl3) the Br- anion of the starting material is replaced by Cl−, in contrast to the K2CO3-CHCl3 system.

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Authors and Affiliations

  1. Institute of Chemistry and Chemical Technology, Academy of Sciences of the Lithuanian SSR, 232600, Vilnius

    R. V. Butkene, G. V. Mikul'skene, O. S. éikher-Lorka & G. -K. K. Kupyatis

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  1. R. V. Butkene
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  2. G. V. Mikul'skene
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  3. O. S. éikher-Lorka
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  4. G. -K. K. Kupyatis
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 520–524, April, 1989.

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Butkene, R.V., Mikul'skene, G.V., éikher-Lorka, O.S. et al. Alkylation of 4-picolinium salts under phase transfer conditions. Chem Heterocycl Compd 25, 433–438 (1989). https://doi.org/10.1007/BF00480760

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  • DOI: https://doi.org/10.1007/BF00480760

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