2,5-Hexanedione → 5-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine

Participants

Reaction Steps

To a solution of 2-amino-5-bromopyridine (89.87 g, 0.5194 mol) in toluene (500 mL) was added 2,5-hexanedione (85.0 mL, 0.724 mol). The reaction flask was equipped with a Dean-Stark apparatus and the solution heated to reflux for 14 h. The cooled reaction solution was extracted with H2O (2×200 mL). The organic layer was added directly to a plug of SiO23″l×2″w and eluted with toluene (250 mL). This treatment removes a significant amount of color from the crude product. The resulting eluent was concentrated to a light amber oil, which solidified upon cooling to provide 128.76 g (99%) of the title compound.

Provenance & Evidence