[N:1]1([CH:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=O)[CH3:15])=[C:9]([N+:17]([O-:19])=O)[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.CC(O)C.Cl.[H][H]>CO>[N:1]1([CH:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]2[CH:12]=[CH:11][C:10]3[N:13]=[C:14]([CH3:15])[N:17]([OH:19])[C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1
A mixture of 4.9 parts of N-[4-[(1H-imidazol-1-yl)phenylmethyl]-2-nitrophenyl]acetamide, 12 parts of 2-propanol, saturated with hydrogen chloride and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of platinium-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in dichloromethane and water and then the solution was neutralized with an ammonium hydroxide solution. The dichloromethane layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (85:15 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 2.2 parts (40.6%) of 6-[(1H-imidazol-1-yl)phenylmethyl]-2-methyl-1H-benzimidazol-1-ol as a residue (compound 219).
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