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

HRID 1936461Notes

Reaction equation

HRID 1936461 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-dddf92dec61d4d0cb6da8535b75aadba
Source dataset
uspto-grants-2002_05
Patent number
US06388084B1

Reaction notes

Loading…