Ethanol → 4-(2-Methyl-1H-imidazo[4,5-C]pyridin-1-YL)benzoic acid
Reaction equation
C(C1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:11]=[C:10]2[CH3:18])=[CH:5][CH:4]=1)#N.[OH-:19].[Na+].[CH2:21]([OH:23])[CH3:22]>>[CH3:18][C:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:22]([C:21]([OH:19])=[O:23])=[CH:4][CH:5]=2)[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:11]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 1-(4-cyanophenyl)-2-methylimidazo[4,5-c]pyridine (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%).