Selenium Dioxide → 2-Phenyl-quinoline-8-aldehyde

Participants

Reaction Conditions

Reaction Steps

8.46 g of 8-methyl-2-phenylquinoline [compare Atwell, G.J. et al., J. Med. Chem. 32, 396-401 (1989)] are mixed with 8.9 g (80 mmol) of selenium dioxide and heated first to 140° C. with stirring, then to 160° C. for 5 hours. The mixture is cooled, a further 2.5 g of selenium dioxide are added and the mixture is stirred at 160° C. for 2.5 hours. It is cooled, stirred with methylene chloride, the solid is filtered off and the filtrate is concentrated. The mixture obtained is purified by flash chromatography on silica gel using toluene/hexane 1:1 and toluene. 3.9 g of beige colored crystals of melting point 100°-102° C. are obtained.

Provenance & Evidence