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

HRID 1187871Notes

Reaction equation

HRID 1187871 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 NH4Cl 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 NH4Cl solution
  3. concentrationThe organic phase was concentrated
  4. customto give the crude product, which
  5. customwas purified by column

Sources & evidence

ORD record
ord-c07e35711fdb48fcbf36467c644a83d0
Source dataset
uspto-grants-2014_03
Patent number
US08673899B2

Reaction notes

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