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

HRID 921968Notes

Reaction equation

HRID 921968 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 (1-2; 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. The reaction mixture was stirred at room temperature for 18 h, cooled, and diluted with ice cold water (500 mL). The resulting precipitated was filtered and dried to obtain the title compound as a white solid; 1H NMR (DMSO-D6, 500 MHz) δ=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. temperaturecooled
  2. customThe resulting precipitated
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-99adc0e5d9be4277939bd3aa84790c69
Source dataset
uspto-grants-2016_03
Patent number
US09278093B2

Reaction notes

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