Hydrochloric Acid → 7-Fluoro-4-hydroxy-1-(2-propen-1-yl)-2(1H)-quinolinone
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:21])=[C:7](C(OCC)=O)[C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[CH2:14])=[CH:4][CH:3]=1.Cl>[OH-].[Na+]>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:21])=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[CH2:14])=[CH:4][CH:3]=1Participants
4
Procedure
Ethyl 7-fluoro-4-hydroxy-2-oxo-1-(2-propen-1-yl)-1,2-dihydro-3-quinolinecarboxylate (4.46 g, 15.3 mmol) was suspended in 2N sodium hydroxide solution (70 ml) and heated at reflux for 4 h. After cooling, the pH was adjusted to ˜pH6 using 2N hydrochloric acid and the resulting precipitate filtered off, washed with water and dried under vacuum to provide the title compound as an off-white solid (2.73 g, 81%).