Methyl iodide → 3-Bromo-5-chloro-1-methylpyridin-2(1H)-one

HRID 895885Notes

Reaction equation

HRID 895885 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:10](=O)([O-])[O-].[K+].[K+].IC>COCCOC>[Br:1][C:2]1[C:3](=[O:9])[N:4]([CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27267913-Bromo-5-chloropyridin-2-ol

Product 1

HCID 223820353-Bromo-5-chloro-1-methylpyridin-2(1H)-oneYield 74.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-bromo-5-chloro-1H-2-pyridone (930 mg, 4.46 mmol), potassium carbonate (1.25 g, 9.1 mmol) and iodomethane (2.8 mL, 45 mmol) in 10 mL of DME was heated to reflux for 18 hr. The mixture was filtered hot and concentrated. The residue was recrystallized from ethyl acetate to give 3-bromo-5-chloro-1-methyl-2-pyridone (740 mg, 74%), mp 162-163° C. HRMS (C6H5BrClNO): Obs. Mass 220.9249. Calcd. Mass 220.9243 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hr
  3. filtrationThe mixture was filtered hot
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9da37b386b744036a22fd1306271d042
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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