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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Alkylation of salts of pyridinols, quinolinols and isoquinolinols

LW Deady, WL Finlayson and CH Potts

Australian Journal of Chemistry 30(6) 1349 - 1352
Published: 1977

Abstract

The ratio of N- to O-alkylation has been determined for reaction of the sodium salts of pyridin-2-ol, 6-methylpyridin-2-ol, pyridin-4-ol, quinolin-2-ol, quinolin-4-ol, 2-methylquinolin-4-ol, isoquinolin-1-ol and 3-methylisoquinolin-1-ol with ethyl iodide and diethyl sulphate in aprotic solvents. N-Alkylation is generally favoured. Reaction at the nitrogen is subject to steric hindrance by adjacent groups (methyl or benzo), but in the benzo-fused compounds this effect is opposed by an electronic one arising from the naphthalene nature of the compounds. This results in a greater charge density on the nitrogen than is the case in the analogous pyridines.

https://doi.org/10.1071/CH9771349

© CSIRO 1977

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