Water → 6-Bromo-8-fluoro-3,4-dihydroquinolin-2(1H)-one
Reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[NH:18][C:17](=[O:20])[CH2:16][CH2:15]2.O>CN(C=O)C>[Br:8][C:12]1[CH:13]=[C:14]2[C:19](=[C:10]([F:9])[CH:11]=1)[NH:18][C:17](=[O:20])[CH2:16][CH2:15]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
NBS (0.62 g, 3.5 mmol) dissolved in DMF (5 mL) was added to a solution of 8-fluoro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 3.2 mmol) in DMF (5 mL) dropwise at 0° C. The resulting reaction mixture was stirred at room temperature for 12 hr before it was treated with water. The precipitated solid was collected through filtration, washed with ether, and dried over vacuum to afford title compound (0.65 g, 85% yield) as a white solid. MS: 244.1 (M+H)+.
Workup
- customThe resulting reaction mixture
- filtrationThe precipitated solid was collected through filtration
- washwashed with ether
- customdried over vacuum
Sources & evidence
- ORD record
- ord-613b7bfc057f4b0e91bdc85ec7895afb
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353081B2
Reaction notes
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