Hydroxylamine → 2',3-Dimethyl-[2,4'-bipyridine]-5-carbaldehyde oxime

Participants

Reaction Steps

To a 5-L four-necked flask equipped with an overhead stirrer, and a thermocouple was charged with 2′,3-dimethyl-[2,4′-bipyridine]-5-carbaldehyde (34d, 1120 mmol), hydrochloro hydroxyamine (34e, 140.1 g, 2016 mmol), and ethanol (1600 mL). The mixture was stirred at 23° C. for 2 h before the addition of NaOAc (183.8 g, 2240 mmol, 2 eq) and iso-propyl acetate (2 L)/water (2 L). The aqueous layer was back-extracted with iso-propyl acetate (2 L) after the layer separation. The combined organic layers were concentrated to almost dryness to afford the crude 2′,3-dimethyl-[2,4′-bipyridine]-5-carbaldehyde oxime (34f) as a brown oil.

Provenance & Evidence