Methyl iodide → 4-Bromo-1-methylpyridin-2(1H)-one

HRID 1640786Notes

Reaction equation

HRID 1640786 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([OH:10])[CH:5]=1.[CH3:11]I>C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][N:7]([CH3:11])[C:6](=[O:10])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178515446HCID 178515446, compound

Product 1

HCID 221323964-Bromo-1-methylpyridin-2(1H)-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (300 mg, 7.5 mmol) in THF (10 mL) was added 4-bromopyridin-2-ol (303 mg, 1.73 mmol) at 0° C. After the resulting mixture was stirred for 1 h, CH3I (491 mg, 3.46 mmol) was added, and the mixture was stirred overnight. The reaction was quenched with aqueous WWI solution. The organic phase was concentrated to give the crude product, which was purified by column to give 4-bromo-1-methylpyridin-2(1H)-one (161 mg, 50%).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction was quenched with aqueous WWI solution
  3. concentrationThe organic phase was concentrated
  4. customto give the crude product, which
  5. customwas purified by column

Sources & evidence

ORD record
ord-15b5224ff06f4be39c952e3539ec1ebf
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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