p-Cyanobenzyl alcohol → N-Hydroxy-4-(hydroxymethyl)benzimidamide

Participants

Reaction Steps

A solution of 4-(hydroxymethyl)benzonitrile (22.43 g, 0.1685 g), hydroxylamine hydrochloride (18.67 g, 0.2689 mol) and NaHCO3 (45.22 g, 0.538 mol) in methanol (250 mL) was heated to reflux overnight. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with additional methanol. The filtrate was evaporated to dryness to afford an off-white solid. The solids were suspended in ˜75 mL hot methanol, then cooled to room temperature and filtered. The filtrate was evaporated to afford N′-hydroxy-4-(hydroxymethyl)benzimidamide (28.5 g) as a white solid. The material was used without further purification. The compound had an HPLC retention time=0.232 min. −Column: CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1=167.3

Provenance & Evidence