Potassium Hydroxide → 6-Bromo-2-(3,5-dimethylphenyl)quinoline

Participants

Reaction Steps

(2-Amino-5-bromophenyl)methanol (22 g, 109 mmol), 3,5-dimethylacetophenone (24.2 g, 163 mmol), RuCl2(PPh3)3 (1.05 g, 1.09 mmol), KOH (11.0 g, 196 mmol) were refluxed in 270 mL of toluene for 18 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with 5% ethyl acetate in hexanes. The product was further purified by Kugelrohr distillation and crystallization from methanol.

Provenance & Evidence