[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9](=O)[CH3:10])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:19][OH:20].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O1CCCC1.O>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9](=[N:19][OH:20])[CH3:10])=[CH:3][CH:2]=1
Next, water (12 ml) and tetrahydrofuran (1.2 ml) were added to 4-(4-pyridyl)-2-butanone (736 mg, 3.96 mmol), and the mixture was stirred at room temperature. Sodium carbonate (483 mg, 4.56 mmol) and hydroxylamine hydrochloride (358 mg, 5.15 mmol) were added to the mixture, the whole was stirred for 1.5 hours, and then ethyl acetate (50 ml) was added to the reaction mixture to dilute it. Sodium hydrogencarbonate was added thereto. After separation, the organic layer was washed with saturated brine (10 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. Cyclohexane was added to the resulting crystals, and the crystals were filtered off to give 4-(4-pyridyl)-2-butanone oxime (584 mg, 90%) as pale yellow crystals.
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