[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[N+:15]([O-])([OH:17])=[O:16].O>OS(O)(=O)=O>[N+:15]([C:7]1[CH:6]=[C:5]([C:1](=[O:4])[CH2:2][CH3:3])[CH:10]=[CH:9][C:8]=1[NH:11][C:12](=[O:14])[CH3:13])([O-:17])=[O:16]To a solution of N-(4-propionylphenyl)acetamide (1.91 g, 10 mmol) in 20 mL of concentrated H2SO4 was added 2 mL 98% HNO3 over 10 minutes while maintain the temperature at −10° C. After stirring for 0.5 h, the mixture was poured into 100 mL of cold water. The precipitate was collected by filtration and washed with water to give the crude product (1.18 g, 50%), which was used directly in the next step.
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