C([N:4](CC)C(C)C)(C)C.O.NN.Cl.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=[NH:25])[NH2:24])=[CH:19][CH:18]=1)([O-:16])=[O:15].[Cl-].[Na+]>CO.C(OCC)(=O)C>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([C:23](=[NH:24])[NH:25][NH2:4])=[CH:21][CH:22]=1)([O-:16])=[O:15]At 0° C., 5.2 ml (29.8 mmol, 3 eq.) of N,N-diisopropylethylamine and 0.62 g (purity 80%, 9.92 mmol, 1.0 eq.) of hydrazine monohydrate were added to a solution of 2.0 g (9.92 mmol) of 4-nitrobenzenecarboximidamide monohydrochloride in 20 ml of methanol, and the mixture was stirred at RT for 64 h. The reaction mixture was then added to 10% strength sodium chloride solution and, after addition of ethyl acetate and phase separation, was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. Yield: 1.7 g (93% of theory)
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