Toluene → HCID 178498494, compound

Participants

Reaction Steps

27 ml of dimethyl acetylenedicarboxylate was added to a solution of 34.4 g of 2-bromoaniline in 200 ml of MeOH placed in a 1 L-flask at room temperature. The mixture was stirred overnight at room temperature. The mixture was concentrated in vacuo to afford a yellow oil. The crude product was added to 200 ml of Ph2O placed in 1 L-flask heated at 250° C. The mixture was stirred for 15 min at the same temperature and then cooled to room temperature. 200 ml of toluene and 200 ml of hexane was added to the mixture. The slurry was stirred for 1 h with cooling at 0 deg C. The resulting solid was filtered, washed with hexane, and dried under vacuum to afford methyl 8-bromo-4-hydroxyquinoline-2-carboxylate as an off-white solid.

Provenance & Evidence