Water → 4-chloro-N'-hydroxybenzenecarboximidamide

Temperature

60 °C

A solution of 50% aqueous sodium hydroxide (2.8 g, 36.34 mmol) was mixed in methanol (20.0 mL). Hydroxylamine hydrochloride (2.55 g, 36.34 mmol) was added and the mixture stirred for 5 minutes. 4-Chlorobenzonitrile (4.0 g, 29.08 mmol) was added and the mixture heated to 60° C. The heterogeneous mixture was stirred at 60° C. for 3 hours. The mixture was poured into water (30 mL) and solids dissolved and a precipitate appeared. The methanol was removed at reduced pressure and remaining solids collected by vacuum filtration. The solids were washed with water (2×10 mL). The 4-chlorobenzamidoxime (4.38 g, 25.6 mmol) was obtained as a white solid. (88% yield).

1. stirringThe heterogeneous mixture was stirred at 60° C. for 3 hours
2. dissolutiondissolved
3. customThe methanol was removed at reduced pressure
4. filtrationcollected by vacuum filtration
5. washThe solids were washed with water (2×10 mL)

ORD record

ord-911568f3cf51437da97eb92602b66dc0

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273037B2