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

HRID 2090327Notes

Reaction equation

HRID 2090327 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[CH:3]=1.[H-].[Na+].CI.[C:13]([O-])(O)=O.[Na+]>CN(C)C=O>[I:1][C:2]1[CH:7]=[CH:6][N:5]([CH3:13])[C:4](=[O:8])[CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178516330HCID 178516330, compound

Product 1

HCID 534080094-Iodo-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodopyridin-2-ol (450 mg, 2.0 mmol, Maybridge, Cat. No. MO07919) in N,N-dimethylformamide (7 mL) was added sodium hydride (120 mg, 3.0 mmol, 60% dispersion in mineral oil) at 0° C., the solution was stirred 5 min., then methyl iodide (250 uL, 4.1 mmol) was added. The reaction mixture was stirred at r.t. for 2 h., and then poured into aqueous NaHCO3 solution, extracted with AcOEt. The organic layer was washed by water and brine, dried over MgSO4, filtered, and concentrated to afford the desired compound which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=235.9.

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 2 h.
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed by water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22d144ff65c44ce4b2ed24a416436673
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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