Water → HCID 21082100, compound

Participants

Reaction Steps

A mixture of (±)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (described in Example B14) (0.000694 mol) and NaCN (0.00139 mol) in DMSO (3.5 ml) was stirred at room temperature for 2 hours, poured out into H2O, basified with K2CO3 (10%) and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 95/5/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.08 g (23%) of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzeneacetonitrile, as a white foam.

Provenance & Evidence