Hydrogen Bromide → 8-Ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one
Reaction equation
[CH2:1]([C:3]1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13]C)[CH:9]=[CH:8]2)[CH3:2].Br.C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[CH2:1]([C:3]1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH3:2]Participants
Procedure
A suspension of 8-ethyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (1.045 g, 5.07 mmol) in glacial acetic acid (10 ml) at rt under argon, was treated with 33% HBr in acetic acid (10 mL). After stirring at rt for 18 h, the solvents were evaporated under reduced pressure. More glacial acetic acid (10 ml) was added to the reaction mixture and the solvent was removed to give a yellow solid. As this residue was placed in water (ca. 50 ml) a white precipitate came out of solution. The pH was adjusted to pH 6-7 by addition of solid sodium hydrogen carbonate. The mixture was then stirred at rt for 2 h, after which the solid was isolated by filtration with suction to give a white damp solid. This product was dried on the sinter with suction for 2 h then dried in a vacuum oven over 18 h at 40° C. to give the title compound as an white solid (0.81 g, 83%).
Workup
- customthe solvents were evaporated under reduced pressure
- additionMore glacial acetic acid (10 ml) was added to the reaction mixture
- customthe solvent was removed
- customto give a yellow solid
- stirringThe mixture was then stirred at rt for 2 h
- customafter which the solid was isolated by filtration with suction
- customto give a white damp solid
- customThis product was dried on the sinter with suction for 2 h
- customthen dried in a vacuum oven over 18 h at 40° C.
Sources & evidence
- ORD record
- ord-f6f620c403094464a135442422787344
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071592B2
Reaction notes
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