Sulfuric Acid → 2-(8-Bromo-5-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acetic acid
Reaction equation
C(O[C:5](=[CH:19][C:20](=[O:22])C)[CH2:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[Br:18])=[O:8])(=O)C.S(=O)(=O)(O)[OH:24]>>[Br:18][C:11]1[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[C:15]2[C:10]=1[NH:9][C:7](=[O:8])[CH:6]=[C:5]2[CH2:19][C:20]([OH:22])=[O:24]Participants
3
Procedure
1-(2-bromo-5-methoxyphenylamino)-1,5-dioxohex-3-en-3-yl acetate (8 g; 21.50 mmol) was added in small portions to concentrated sulfuric acid (30 ml) at room temperature and the mixture was stirred for 30 min. Ice was added to the reaction mixture and the formed precipitate was filtered, washed with water and dried over phosphorus pentoxide under reduced pressure to afford 5.97 g (89%) of 2-(8-bromo-5-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acetic acid as a grey solid.
Workup
- additionIce was added to the reaction mixture