Water → 6-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

HRID 1774838Notes

Reaction equation

HRID 1774838 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]2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 709774606-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONEYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 0° C., NBS (0.62 g, 3.5 mmol) was added dropwise to a solution of 8-fluoro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 3.2 mmol) in DMF (5 mL). The resulting reaction mixture was stirred at room temperature for 12 hours before it was treated with water. The precipitated solid was collected through filtration, washed with ether, and dried in a vacuum to afford title compound (0.65 g, 85%) as a white solid. MS: 244.1 (M+H+)+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe precipitated solid was collected through filtration
  3. washwashed with ether
  4. customdried in a vacuum

Sources & evidence

ORD record
ord-846e6a1d337d47f78e8799f0bafc13e7
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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