[C:1]1([C:7]2[O:11][C:10]([C:12]#[N:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:15][OH:16].[OH-].[K+]>C(O)C>[C:1]1([C:7]2[O:11][C:10]([C:12](=[N:15][OH:16])[NH2:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1A mixture of 10 g (0.059 mole) of 5-phenyl-2-furonitrile, 4.1 g (0.060 mole) of hydroxylamine hydrochloride, 4.0 g (0.060 mole) of potassium hydroxide, and 150 ml of absolute ethanol was refluxed for 21/2 hours, cooled to room temperature, and then added to 750 ml of ice/H2O. the resulting solid was washed in water and dried at 60° to yield 10 g (84%), m.p. 118°-120°.
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