Hydrochloric Acid → HCID 57061813, compound

Participants

Reaction Steps

8-Bromo4-quinoline carboxylic acid methyl ester, D16 (E. R. Buchman et al., J. Amer. Chem. Soc., 1946, 68, 2692), (0.712 g), (1-ethoxyvinyl)tributyltin (1.60 g) and tetrakis(triphenylphosphine)palladium (O) in 1,4-dioxane (50 ml) were heated at reflux for 16 h. The reaction mixture was cooled to ambient temperature, HCl (5M, 1 ml) and water (15 ml) added and the resulting mixture stirred for 3 h. The solvent was removed at reduced pressure, the residue suspended in EtOAc and the solid removed by filtration. The organic phase was washed with saturated sodium bicarbonate, dried (Na2SO4), removal of the solvent under reduced pressure gave a dark oil which was chromatographed (silica gel, hexane diethyl ether) to give the title compound (0.500 g).

Provenance & Evidence