Methyl iodide → HCID 90037108, compound

HRID 1055407Notes

Reaction equation

HRID 1055407 reaction equation
CI.[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[C:7]2[CH3:15].[C:16]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:16])[C:9](=[O:14])[CH:8]=[C:7]2[CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 63247046-fluoro-4-methylquinolin-2(1H)-one

Product 1

HCID 90037108HCID 90037108, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

MeI (130 mg, 0.914 mmol) was added into a suspension of 6-fluoro-4-methylquinolin-2(1H)-one (135 mg, 0.762 mmol) and Cs2CO3 (248 mg, 0.762 mmol) in DMF (10 mL). The reaction mixture was stirred overnight and partitioned between Na2CO3 solution and EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated. The resulting solid was washed with hexanes and dried to give 6-fluoro-1,4-dimethylquinolin-2(1H)-one (100 mg, 68%) as a white solid which was used without purification.

Workup

  1. custompartitioned between Na2CO3 solution and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. washThe resulting solid was washed with hexanes
  6. customdried

Sources & evidence

ORD record
ord-425999adc38f4c26b59bcd997f78d920
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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