Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[ClH:10].[CH2:11]([NH2:13])C.[OH-:14].[Na+].C(N(CC)CC)C.C(OC(=O)C)(=[O:25])C.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O.C(O)C.CN(C)C1C=CN=CC=1>[Cl:10][C:2]1[C:3](/[CH:4]=[CH:11]/[N+:13]([O-:25])=[O:14])=[CH:6][CH:7]=[CH:8][N:9]=1To 2-chloronicotinaldehyde (2.8 g, 19.8 mmol) in nitromethane (6.1 g) was added ethylamine hydrochloride (100 mg, 1.2 mmol) and NaOH (25 mg) in ethanol (1.5 mL). The mixture was stirred for 1 hour and concentrated. The crude was dissolved in CH2Cl2 (30 mL) and treated with triethylamine (2.8 g, 28 mmol), 4-(dimethylamino)pyridine (20 mg) and acetic anhydride (2.0 g, 20 mmol) at 0° C. The mixture was stirred for 15 minutes and concentrated saturated NaHCO3(aq) was added, and the precipitates were collected to afford the title compound.
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