Water → 6-Bromo-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 530338Notes

Reaction equation

HRID 530338 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][CH:3]=1.C1C(=O)N([Br:21])C(=O)C1.O>CN(C=O)C.CCOC(C)=O>[Br:21][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[F:1])[N:9]([CH3:12])[C:8](=[O:13])[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 224137757-Fluoro-1-methyl-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 866791306-Bromo-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-oneYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice cold solution of 7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one (16.0 g, 89.4 mmol) in DMF (200 mL) was added NBS (16.0 g, 89.4 mmol). After the addition, the reaction mixture was warmed up to room temperature and stirred for 3 hr. After LC-MS analysis indicated the completion of reaction, the mixture was diluted with EtOAc (500 mL) and poured into water (500 mL). The aqueous layer was then extracted with EtOAc (200 mL, 3×) and the combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give crude title compound as oil (18.0 g, 78% yield). It was used in the next step without further purification.

Workup

  1. additionAfter the addition
  2. customthe completion of reaction
  3. extractionThe aqueous layer was then extracted with EtOAc (200 mL, 3×)
  4. washthe combined organic layers were washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f62403e997c44fda0fd95b0449db12b
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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