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

HRID 1521671Notes

Reaction equation

HRID 1521671 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 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (157-2; 8.30 g, 50.10 mmol) in N,N-dimethylformamide (250 mL) was added N-bromosuccinimide (9.80 g, 55.10 mmol) in N,N-dimethylformamide (120 mL) at 0° C. Reaction mixture was allowed to stir at room temperature for 18 h, then cooled and diluted with ice cold water (500 mL). The resulting precipitated was filtered and dried to obtain title compound (white solid). 1H NMR (DMSO-D6, 500 MHz) 6=10.20 (s, 1H), 7.37 (dd, J=2.0 Hz, JHF=10.0 Hz, 1H), 7.26 (s, 1H), 2.93 (t, J=7.0 Hz, 2H), 2.47 (t, J=7.5 Hz, 2H).

Workup

  1. customReaction mixture
  2. temperaturecooled
  3. customThe resulting precipitated
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-d954e5f298b14c0b87995107325d6721
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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