[N+:1]([O-])([OH:3])=[O:2].[CH2:5]([O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)[CH3:6].[N:17]#[C:18][NH2:19]>C(O)C>[N:1]([OH:3])=[O:2].[CH2:5]([O:7][C:8]([C:9]1[CH:10]=[C:11]([NH:15][C:18]([NH2:19])=[NH:17])[CH:12]=[CH:13][CH:14]=1)=[O:16])[CH3:6]Nitric acid (70%, 6.66 mL) is added to a mixture of 3-amino benzoic acid ethyl ester (17.21 g, 104 mmol) and cyanamide (50% in water, 12.1 mL, 156 mmol) in 50 mL of ethanol. The reaction mixture is heated for 24 hours under reflux. It is then cooled to room temperature and filtered. The solid is washed with water, ether and dried to give 3-ethoxycarbonyl-phenyl-guanidine nitrite as a gray solid; ESI-MS (m/z): 208.1 (M+-HNO3+H).
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