Ethanol → 4-(2-Methyl-1H-imidazo[4,5-C]pyridin-1-YL)benzoic acid

反応式

[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]>O>[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]=1

参加物

実験手順

A mixture of 4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzonitrile (see EP-0310386) (12.0 g, 51.3 mmol) and sodium hydroxide (22.0 g, 0.55 mmol) in a mixture of ethanol (55 ml) and water (55 ml) was heated under nitrogen at reflux for 1.5 hours, cooled and concentrated under reduced pressure. The brown residue was dissolved in ice-water and glacial acetic acid (33 ml) was added. The resulting precipitate was collected, washed with water and dried under vacuum at 70° C. to give the title compound (9.1 g, 70%) as a buff coloured solid which as characterised by its 1H-NMR spectrum. 1H NMR (DMSO-d6), 2.50(3H,s), 7.25(1H,d,J=5 Hz), 7.72(2H,d,J=8 Hz), 8.16(2H,d,J=8 Hz), 8.30(1H,d,J=5 Hz), 8.92(1H,s).