3-Nitrobenzonitrile → N'-hydroxy-3-nitrobenzenecarboximidamide

Participants

Reaction Steps

In a 500-ml flask, place 30.6 g (0.21 m) of 3-nitrobenzonitrile (3a; R2=3-nitrophenyl) and 150 ml of methanol and stir to a solution. Add 48 g (0.22 m) of 25 wt % sodium methoxide in methanol slowly and stir at room temperature for 1.5 hrs. Add 22.5 ml of acetic acid to make pH of reaction mixture around 6. Add 18.1 g (0.22 m) of sodium acetate and 22 g (0.32 m) of hydroxylamine hydrochloride. After a few minutes with stirring, the reaction mixture becomes thick yellow slurries. Stir the slurries at room temperature for 1 hr. Add 130 ml of water and stir for 15 min. Collect solid, wash with water and dry in air to give 30.5 g (80%) of 3-nitrobenzamidoxime (9a; R=3-nitrophenyl).

Provenance & Evidence