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

HRID 1521629Notes

Reaction equation

HRID 1521629 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[Br:13]N1C(=O)CCC1=O>CN(C)C=O>[Br:13][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([F:1])[CH:3]=1)[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Participants

4

Reactant 2

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

Product 1

HCID 709774606-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (109-2; 7 g, 0.0424 mol) in N,N-dimethylformamide (30 mL) was added N-bromosuccinimide (9.06 g, 0.050 mol) portion wise at 0° C. Reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was concentrated and diluted with ice cold water (150 mL) with constant stirring and the solid residue was filtered and dried to obtain the title compound. MS (M+1): 245.1

Workup

  1. customReaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ice cold water (150 mL)
  4. stirringwith constant stirring
  5. filtrationthe solid residue was filtered
  6. customdried

Sources & evidence

ORD record
ord-08b05b465be4416b8879606fd84cdfbc
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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