Methyl iodide → 5-Bromo-1,3-dimethylpyridin-2(1H)-one

HRID 1487271Notes

Reaction equation

HRID 1487271 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[N:6][CH:7]=1.[C:10](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5](=[O:8])[N:6]([CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178422464HCID 178422464, compound

Product 1

HCID 122726645-Bromo-1,3-dimethylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-bromo-2-hydroxy-3-methyl pyridine A1 (1.000 g; 5.053 mmol) and potassium carbonate (1.397 g; 10.105 mmol) in DMF (5.000 ml) is carefully added iodomethane (0.346 ml; 5.558 mmol). The reaction mixture is stirred overnight (16 h) at room temperature. The reaction mixture is then quenched with 10% ammonia solution (10 ml) and 30 ml water is added. It is extracted with 3×50 ml EtOAc. The combined organic layer is dried with Na2SO4, filtered and concentrated under reduced pressure to afford the product.

Workup

  1. customThe reaction mixture is then quenched with 10% ammonia solution (10 ml) and 30 ml water
  2. additionis added
  3. extractionIt is extracted with 3×50 ml EtOAc
  4. dry with materialThe combined organic layer is dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford the product

Sources & evidence

ORD record
ord-9ea9cd040f4f439192588fa5ee0006d5
Source dataset
uspto-grants-2016_08
Patent number
US09428515B2

Reaction notes

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