Yield:51049-14-0 20%

Reaction Conditions:

with sodium tetrachloroaurate(III) dihyrate in ethanol at 70; for 24 h;

Steps:

General procedure for the alkylation/gold-catalyzed annulation reactions of anilines with propargylic bromide derivatives: to a solution of aniline 1 (2.0 mmol) in absolute ethanol (2 mL) were added propargylic bromide 2 (0.66 mmol) and NaAuCl₄·2H₂O (0.05 mmol). The resulting mixture was heated at 70 °C for 24 h. The reaction was monitored by TLC. After cooling, the solvent was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and extracted three times with a saturated solution of NaHCO₃. The combined aqueous extracts were extracted three times with ethyl acetate. The combined organic extracts were dried (Na₂SO₄) and evaporated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexanes-ethyl acetate mixtures) to give quinoline 4.

References:

Alfonsi, Maria;Arcadi, Antonio;Chiarini, Marco;Marinelli, Fabio [Tetrahedron Letters,2011,vol. 52,# 40,p. 5145 - 5148] Location in patent:experimental part