[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]#[N:19])=[CH:4][CH:3]=1.[NH2:20][OH:21].Cl.C([O-])([O-])=O.[K+].[K+].O>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18](=[N:20][OH:21])[NH2:19])=[CH:4][CH:3]=1To a suspension of 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetonitrile (0.13 mol, 34.0 g) in absolute EtOH (300 mL) was added NH2OH.HCl (0.32 mol, 22.1 g) and K2CO3 (0.32 mol, 44.1 g), respectively. The mixture was stirred at r.t. overnight, filtrated, and washed with EtOH for 3 times. The EtOH-filtrate was concertrated to small volume, and the precipitation was collected by filtration, to give one partial products. The solid was dispersed into water, sonicated for 10 mins, filtrated, washed with water, and dried in vacuo, to give another partial products. Combined two portions products added up to 25.0 g (65.4%). m/e+=301 (M+H+).
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