Hydroxyamine hydrochloride → HCID 9584179, compound

Participants

Reaction Steps

A mixture of 4-(1,3-dioxolan-2-yl)benzonitrile (16.4 g, 93.6 mmol), hydroxylamine hydrochloride (9.76 g, 140 mmol) and sodium bicarbonate (15.7 g, 187 mmol) in MeOH (100 mL) was heated to reflux for 4 hr. After cooling to RT, the reaction mixture was filtered and the filtrate was concentrated to provide solids that were collected by filtration and washed with cold methanol to provide (Z)-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide (16 g, 76.8 mmol). The compound had an HPLC retention time=0.38 min. —CHROMOLITH® SpeedROD 4.6×30 mm. flow=5 mL/min (2 min. gradient); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=209.2

Provenance & Evidence