Thionyl Chloride → (+/-)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4(3-chlorophenyl)-1-methyl-2(1H)-quinolinone

Participants

Reaction Steps

A mixture of (±)-4-(3-chlorophenyl)-6-[hydroxy[4-(hydroxymethyl)phenyl](1-methyl-1H-imidazol-5yl)methyl]-1-methyl-2(1H)-quinolinone (described in Example B9) (0.000823 mol) in thionyl chloride (4 ml) was kept at room temperature for 2 hours. The solvent was evaporated till dryness. The residue was taken up in H2O. EtOAc was added. The mixture was basified with K2CO3 (10%) and extracted. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated, yielding 0.43 g (>100%) of (±)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4(3-chlorophenyl)-1-methyl-2(1H)-quinolinone.

Provenance & Evidence