Methyl iodide → 3-Bromo-1-methyl-1,2-dihydropyridin-2-one

HRID 895899Notes

Reaction equation

HRID 895899 reaction equation
[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.[C:9](=O)([O-])[O-].[K+].[K+].IC>COCCOC>[Br:1][C:2]1[C:3](=[O:8])[N:4]([CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 8185493-Bromo-2-hydroxypyridine

Product 1

HCID 130240253-Bromo-1-methyl-1,2-dihydropyridin-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-bromo-1H-2-pyridone (740 mg, 4.25 mmol), potassium carbonate (1.18 g, 8.5 mmol) and iodomethane (2.65 mL, 42.5 mmol) in DME (10 mL) was heated to reflux overnight. The mixture was filtered, washing with ethyl acetate and the filtrate was evaporated to dryness. The residue was purified by dry column chromatography over 27 g of silica gel, eluting with ethyl acetate to give 3-bromo-1-methyl-2-pyridone (0.63 g, 79%). LRMS (electrospray), positive ion, 188 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtered
  4. washwashing with ethyl acetate
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was purified
  7. customby dry column chromatography over 27 g of silica gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a611c79a75544c1b95ffba957532269e
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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