Sodium Hydroxide → HCID 137190312, compound

Participants

Reaction Conditions

Reaction Steps

5-(2-Chloro-benzyloxy)-pyridine-2-carbaldehyde (which may be prepared as described in Preparation of Intermediate 7; 2.06 g, 8.3 mmol) was suspended in 9:1 EtOH/H2O (20 mL) and hydroxylamine hydrochloride (1.45 g, 20.9 mmol) was added. A solution of 3.25 M NaOH in 9:1 EtOH/H2O (6.5 mL, 21.1 mmol) was added slowly dropwise. The mixture was heated under reflux for 2.5 h and then cooled to 0° C. The pH was adjusted to 4 by the addition of glacial AcOH. The precipitate was filtered off to give 5-(2-chloro-benzyloxy)-pyridine-2-carbaldehyde oxime (1.5 g, 69%) as an off-white solid.

Provenance & Evidence