Acetic Anhydride → 3-(4-Nitrophenyl)pyridin-2(1H)-one
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N+:12]([O-])[CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(OC(=O)C)(=[O:19])C>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:19])[NH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
3
Procedure
3-(4-Nitrophenyl)pyridine-1-oxide (P2, 2.5 g, 11.6 mmol) was stirred at reflux in acetic anhydride (25 mL) for 18 hours, then allowed to cool. The reaction mixture was concentrated and concentrated hydrochloric acid (25 mL) was added. The solution was stirred at reflux for 4 hours, then allowed to cool. The reaction mixture was poured onto ice/water and filtration followed by drying under high vacuum afforded the title compound as a solid.
Workup
- temperatureto cool
- concentrationThe reaction mixture was concentrated
- additionconcentrated hydrochloric acid (25 mL) was added
- temperatureat reflux for 4 hours