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

HRID 1713095Notes

Reaction equation

HRID 1713095 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9]I>CN(C=O)C.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2](=[O:1])[N:3]([CH3:9])[CH:4]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178515818HCID 178515818, compound

Product 1

HCID 130240275-Bromo-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hydroxy-5-bromo-pyridine (3.00 g, 17.3 mmol) in anhydrous DMF (25 mL) is added MeI (2.95 g, 20.76 mmol, 1.2 eq.). The mixture is stirred overnight at rt. The solution is diluted with EtOAc (200 mL) and extracted with H2O (4×100 mL). The organic extract is dried over Na2SO4 and the solvent removed under reduced pressure. The crude product is purified by silica gel chromatography eluting first with hexane/acetone (4:1) followed by elution with hexane/acetone (1:1) to yield the title compound. MS (+VE) m/z 188.02 (M++1).

Workup

  1. extractionextracted with H2O (4×100 mL)
  2. extractionThe organic extract
  3. dry with materialis dried over Na2SO4
  4. customthe solvent removed under reduced pressure
  5. customThe crude product is purified by silica gel chromatography
  6. washeluting first with hexane/acetone (4:1)
  7. washfollowed by elution with hexane/acetone (1:1)

Sources & evidence

ORD record
ord-a43cb3caec75407883edf444a47dcb8f
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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