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

HRID 1191800Notes

Reaction equation

HRID 1191800 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 (80 mg, 2 mmol) in THF (10 mL) was added 4-bromopyridin-2-ol (80 mg, 0.46 mmol) at 0° C. The resulting mixture was stirred for 1 h. Then CH3I (355 mg, 2.5 mmol) was added to the above mixture, 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 (42.3 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-51f8b81e7e5c4d1b903f67468398af07
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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