An efficient preparation of 2,2':4,':4',4'Flushing, New York 11367-quaterpyridyl (qpy) from 4,4'-bipyridine is described, using palladium on charcoal. Conditions are described for the selective methylation of the nitrogen atoms present. This has allowed the preparation of mono- and dimethylquaternary salts that retain an a-diimine site for complexation to a metal. These quaternary salts can be used to prepare complexes in which metal ions are coordinated to viologen-type ligands. Electrochemical and spectroscopic measurements of the diquaternary salt derived from qpy suggest that it behaves as two separate or weakly interacting monoquat moieties. © 1990, American Chemical Society. All rights reserved.