Cl.[NH2:2][OH:3].C([O-])([O-])=O.[Na+].[Na+].[C:10]([O:14][C:15](=[O:25])[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=1)([CH3:13])([CH3:12])[CH3:11]>O.CO>[C:10]([O:14][C:15](=[O:25])[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[NH:24])[NH:2][OH:3])[CH:18]=1)([CH3:13])([CH3:11])[CH3:12]Hydroxylamine hydrochloride (179 mg, 2.60 mmol) and Na2CO3 (138 mg, 1.30 mmol) was dissolved in 1 mL water. A solution of (3-cyano-phenyl)-carbamic acid tert-butyl ester (560 mg, 2.60 mmol) in 10 mL of methanol was added and the combined solution was stirred at reflux overnight. The solvent was removed and the resulting precipitate was extracted with water and ethyl acetate to yield [3-(N-hydroxycarbamimidoyl)-phenyl]-carbamic acid tert-butyl ester which was used without further purification.
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