Potassium Hydroxide → 5-(2-Nitrophenyl)-2-furamidoxime Hydrochloride

Participants

Reaction Steps

A mixture of 5-(2-nitrophenyl)-2-furonitrile (34 g, 0.16 mole), KOH (9.5 g, 0.17 mole), hydroxylamine hydrochloride (11.5 g, 0.165 mole) and absolute alcohol (400 ml) was heated under reflux for 2 hours. The reaction mixture was cooled in ice, and the insoluble material was collected by filtration. The solvent was removed on a rotary evaporator, and the residual oil (44 g) was triturated with water several times. It was dissolved in anhydrous ether (ca. 2l. ) and the insoluble material was removed by filtration. Gaseous HCl was introduced into the filtrate yielding a solid that was collected by filtration and washed with anhydrous ether to give 33 g (73%). An analytical sample, m.p. 205°-206°, was obtained by recrystallization from isopropanol.

Provenance & Evidence