C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][OH:9].[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]>CCOC(C)=O>[OH:9][N:8]=[C:17]([NH2:18])[C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:20][CH:19]=1Potassium carbonate and hydroxylamine hydrochloride were added to an ethanolic solution of 4-nitrobenzonitrile. The solution was refluxed at 80° C. for 5 hours. After completion of the reaction the solvent was evaporated and the crude so obtained was dissolved in EtOAc and washed with water, brine, then dried by sodium sulfate and concentrated to give a solid. It was the purified by column chromatography and further recrystallized from EtOAc: petroleum ether to obtain the title product in 86.88% yield. 1H NMR (DMSO-d6) δ: 6.071 (s, 2H, NH2) 8.24 (d, 2H, CH), 8.317 (d, 2H, CH), 10.138 (S, 1H, OH), ms (m/z) 180 (M−−H).
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