
TY  - JOUR
A1  - Deady, LW 
A1  - Finlayson, WL 
A1  - Potts, CH 
T1  - Alkylation of salts of pyridinols, quinolinols and isoquinolinols
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1977
VL  - 30
IS  - 6
SP  - 1349
EP  - 1352
KW  - 
UR  - https://doi.org/10.1071/CH9771349 
N2  - 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. 
ER  -

