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

Participants

Reaction Conditions

Reaction Steps

NaBH4 (0.00413 mol) was added portionwise at 0° C. to a mixture of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6 quinolinyl]hydroxy (1-methyl-1H-imidazol-5yl)methyl]benzaldehyde (described in Example B6).(0.00207 mol) in THF (10 ml). The mixture was stirred at 0° C. for 30 minutes, poured out into H2O and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 90/10/0.5; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.5 g (50%) of (±)-4-(3-chlorophenyl)-6-[hydroxy[4-(hydroxymethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone, mp. 273° C.

Provenance & Evidence