3-Pyridinecarboxaldehyde → 3-Pyridine aldoxime

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Reaction Steps

3-Pyridinecarboxaldehyde oxime was prepared by treating 3-pyridinecarboxaldehyde (10 mL, 106 mmol) with hydroxylamine hydrochloride (8.10 g, 117 mmol) and 50% aqueous sodium hydroxide (2 mL) in ethanol (100 mL) and water (200 mL) for 17 hours. The solution was adjusted to pH 14 with the addition of 50% (w/w) aqueous sodium hydroxide. The solution was extracted with several portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 8.3 g of a white solid. The aqueous layers were combined and back-extracted with chloroform (5×1 L) to yield additional product. The total amount of 3-pyridinecarboxaldehyde oxime obtained was 12.24 g.

Provenance & Evidence