Methyl iodide → 3-Bromo-5-chloro-1-methylpyridin-2(1H)-one
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas heated
- temperatureto reflux for 18 hr
- filtrationThe mixture was filtered hot
- concentrationconcentrated
- customThe residue was recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-fafc29b3859d46bd939a1a61e51f9b4a
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06388084B1
Reaction notes
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