Sodium Hydroxide → 3,5-Dichloro-4-pyridinecarbaldehyde oxime

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3,5-dichloro-4-pyridinecarbaldehyde (6.50 g, 36.9 mmol) in ethanol (55 mL) was added a solution of sodium hydroxide (1.77 g, 44.3 mmol) and hydroxylamine hydrochloride (3.08 g, 44.3 mmol) in water (30 mL). The suspension was heated to 90° C. The mixture was stirred at 90° C. for approximately 6.5 hours and then concentrated. Water was added and the resulting solid was isolated by filtration and dried under a nitrogen stream at 45° C. over phosphorus pentoxide to afford 3,5-dichloro-4-pyridinecarbaldehyde oxime (6.38 g, 33.4 mmol, 91%). 1H-NMR (400 MHz, DMSO-d6) δ 13.31 (s, 1H), 8.68 (s, 2H), 8.24 (s, 1H).

Provenance & Evidence