[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17].[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13](=[N:16][OH:17])[NH2:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1A mixture of 51 g (0.25 mole) of 5-(p-chlorophenyl)-2-furonitrile, 19 g (0.27 mole) of hydroxylamine hydrochloride, 18 g (0.27 mole) of potassium hydroxide and 750 ml of absolute ethanol was heated under reflux for 1 hour. The reaction mixture was concentrated on a rotary evaporator and cooled in ice overnight. The solid was collected by filtration and washed with anhydrous ether to give 43 g (73%). Two recrystallizations from absolute ethanol gave an analytical sample, m.p. 167°-169°.
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