Ammonium Hydroxide → (+/-)-6-[(1H-imidazol-1-yl)phenylmethyl]-4-phenyl-2(1H)-quinolinone

Participants

Reaction Conditions

Reaction Steps

A mixture of intermediate (1-c) (22.85 g) and aluminium chloride (48 g) in chlorobenzene (200 ml) was heated at 95° C. overnight. The mixture was cooled, poured into ice water, basified with NH4OH and evaporated till dryness. The residue was taken up in DCM and ethanol. The residue was filtered and evaporated. The residue was taken up in DCM and stirred with HCl 3N overnight. The mixture was extracted, the aqueous layer was washed with ethyl acetate, basified with NH4OAc and then extracted with ethyl acetate and the organic layer was dried (MgSO4) and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 95/5/0.05) (35-70 μm). The pure fractions were collected and evaporated, yielding 2.13 g (16%) of (±)-6-[(1H-imidazol-1-yl)phenylmethyl]-4-phenyl-2(1H)-quinolinone; mp. 253.0° C. (comp. 1).

Provenance & Evidence