Boron tribromide → HCID 131718775, compound

Participants

Reaction Steps

A solution of boron tribromide in dichloromethane (1:2, 2 ml) was dropwise added to a solution of 4-(2-chlorophenyl)-3-(2,3-dimethoxycinnamoylamino)-6,8-dimethylquinoline (0.94 g) in dichloromethane (15 ml) under ice-cooling and stirring. After being stirred for 30 minutes under ice-cooling, and further for 1.5 hours at room temperature, the mixture was poured into ice water. The solution was made neutral with a sodium hydrogen carbonate saturated solution and was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was removed, and the residue was dissolved into ethyl acetate (5 ml), to which 4N HCl-ethyl acetate solution (2 ml) was added to give crystals of 4-(2-chlorophenyl)-3-(2,3-dihydroxycinnamoylamino)-6,8-dimethylquinoline hydrochloric acid salt hydrate (0.85 g, 83.3%). The crystals were recrystallized from ethanol to obtain yellowish needles.

Provenance & Evidence