Acetic Acid → (+/-)-4-(3-chlorophenyl)-6-[hydroxy[4[[(2-methoxyethyl)amino]methyl]phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)quinolinone

Participants

Reaction Steps

A mixture of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde (described in Example B6) (0.000207 mol), 2-methoxy-ethanamine (0.000517 mol) and acetic acid (0.0000207 mol) in acetonitrile (2 ml) was stirred at room temperature for 2 hours. NaBH3CN (0.000517 mol) was added and the resulting mixture was stirred at room temperature overnight. After addition of water and extraction with EtOAc, the solvent was evaporated. The residue was purified by HPLC. The product fractions were collected and the solvent was evaporated, yielding 0.008 g (7.13%) of (±)-4-(3-chlorophenyl)-6-[hydroxy[4[[(2-methoxyethyl)amino]methyl]phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)quinolinone, MS (ESI) m/z:543, 545 (MH+).

Provenance & Evidence