N-Ethylaniline → HCID 19029092, compound

Participants

Reaction Steps

A mixture of 2,6-dimethyl-N-phenyl-4-chloropyridinium chloride (previously reported in Annalen, 1958, 617, 181-202) (2.19 g, 10 mM), N-ethylaniline (3.6 g, 30 mM) and ethanol (100 ml) was heated under reflux for 30 minutes. The solvent was removed by evaporation and the resultant syrup was purified by flash chromatography (Merck 9385 silica column, 180 g) using a 1:19 v/v mixture of methanol/methylene chloride as eluant. The resultant syrup was further purified by flash column chromatography using a neutral alumina column (ICN type N32-63, 150 g) and eluting with an increasing gradient (0-5% v/v) of methanol in dichloromethane. There was thus obtained 2,6-dimethyl-4-(N-ethylanilino)-N-phenylpyridinium chloride (1.9, 56% yield) as a pale orange glass; microanalysis, found: C,70.7; H,6.5; N,7.6; Cl,9.7%; C21H23N2Cl .H2O requires: C,70.7; H,7.0; N,7.85; Cl, 9.93%; NMR: 1.2-1.3(3H, t,CH2CH3), 2.1(6H,5 pyridine-CH3), 3.9-4.05(2H,q,CH2CH3), 6.7-7.1(2H,br, pyridine-3H and -5H), 7.35-7.7 (10H, complex, aromatic).

Provenance & Evidence