[C:1](O)(=O)[CH3:2].[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][N:13]=[C:14]([NH2:19])[CH2:15][O:16]CC)[CH:9]=[CH:10][CH:11]=1.[N:20]([O-])=O.[Na+].[OH2:24]>C1COCC1>[CH2:1]([O:24][C:15]([C:14]1[N:19]=[N:20][N:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[CH:7]=2)[N:13]=1)=[O:16])[CH3:2]12.0 mL (210 mmol) acetic acid was added to a solution of 12.0 g (52.7 mmol) N′-(3-chloro-phenyl)-2-ethoxyacetohydrazonamide in 120 mL THF. The mixture was heated to 85° C. and a solution of 4.36 g (63.2 mmol) sodium nitrite in 12 mL water was added over 4 h. After stirring for 1 h at 85° C., the mixture was cooled to RT. The solvent was evaporated. The residue was dissolved in EtOAc and extracted with aqueous sodium bicarbonate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography eluted with hexane/EtOAc (90:10).
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