N-Bromosuccinamide → 6-Bromo-5-fluoro-3,4-dihydro-1H-quinolin-2-one

HRID 1521658Notes

Reaction equation

HRID 1521658 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.[Br:13]NC(=O)CCC(N)=O>CN(C)C=O>[Br:13][C:11]1[C:2]([F:1])=[C:3]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:12])[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 227369425-Fluoro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 709801486-Bromo-5-fluoro-3,4-dihydro-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-fluoro-3,4-dihydroquinolin-2(1H)-one (146-4; 0.45 g, 0.00272 mol) in N,N-dimethylformamide (10 mL) was added N-bromosuccinamide (0.53 g, 0.0029 mol). Reaction mass was allowed to stir for overnight. Ice cold water was added to reaction mass. The solid separated was filtered and dried thoroughly to obtain the title compound. MS (M+1): 246.0.

Workup

  1. customReaction mass
  2. additionIce cold water was added to reaction mass
  3. customThe solid separated
  4. filtrationwas filtered
  5. customdried thoroughly

Sources & evidence

ORD record
ord-80f57e261f5a44dcac8d28ddc0847a22
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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