[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=2)[C:10]([OH:12])=O)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].C(Cl)CCl.ON1C2N=CC=CC=2N=N1.[C:38]([NH:41][NH2:42])(=[O:40])[CH3:39]>CN(C=O)C>[C:38]([NH:41][NH:42][C:10](=[O:12])[C:9]1[CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH:8]=1)(=[O:40])[CH3:39]A screw-cap vial was charged with 3-morpholino-5-nitrobenzoic acid (0.250 g, 0.991 mmol), sodium bicarbonate (0.250 g, 2.97 mmol), EDC (0.285 g, 1.487 mmol), 1-hydroxy-7-azabenzotriazole (0.202 g, 1.487 mmol), acetic hydrazide (0.088 g, 1.189 mmol), and DMF (2.0 mL). The orange solution was stirred at 23° C. for 18 h, then partitioned between EtOAc and water. The organic phase was washed with brine, dried over magnesium sulfate, and concd, affording N′-acetyl-3-morpholino-5-nitrobenzohydrazide as an orange oil. Mass Spectrum (ESI) m/e=309.2 (M+1).
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