[CH:1]([C:3]1[N:4]=[C:5]([NH:14][CH3:15])[S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=O.[NH2:16][OH:17]>CO>[OH:17][N:16]=[CH:1][C:3]1[N:4]=[C:5]([NH:14][CH3:15])[S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1A solution of 4-formyl-2-methylamino-5-(4-pyridyl)thiazole (0.9 g) in methanol (15 ml) was added to a 1N-methanolic hydroxylamine solution (5.8 ml) at ambient temperature with stirring, which was continued under the same condition for 2 hours. The precipitate was collected by filtration and recrystallized from an aqueous tetrahydrofuran to afford 4-hydroxyiminomethyl-2-methylamino-5-(4-pyridyl)thiazole (1.02 g).
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