[CH3:1][C:2]1[N:3]([C:11]2[CH:18]=[CH:17]C(C#N)=[CH:13][CH:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[OH-:19].[Na+].[CH2:21]([OH:23])[CH3:22]>>[CH3:1][C:2]1[N:3]([C:11]2[CH:18]=[CH:17][C:22]([C:21]([OH:19])=[O:23])=[CH:13][CH:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1A mixture of 4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzonitrile (12.0 g, 51.3 mmol) and 40% aqueous sodium hydroxide (55 ml) in absolute ethanol (55 ml) was heated at reflux for 11/2 hours. The solvent was removed under reduced pressure, and the brown residue was dissolved in water. The solution was chilled to 0° C. by the addition of ice. Glacial acetic acid (ca 33 ml) was added slowly. The buff solid which precipitated was filtered off, washed with water, and dried in vacuo at 70° C. Yield 9.14 g (70%).
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