Methyl iodide → 3-Iodo-4-methoxy-1-methylpyridin-2(1H)-one

HRID 19659Notes

Reaction equation

HRID 19659 reaction equation
O[C:2]1[C:7]([I:8])=[C:6]([OH:9])[CH:5]=[CH:4][N:3]=1.[C:10]([O-:13])([O-])=O.[Cs+].[Cs+].[CH3:16]I>CN(C=O)C>[CH3:2][N:3]1[CH:4]=[CH:5][C:6]([O:9][CH3:16])=[C:7]([I:8])[C:10]1=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 178516519HCID 178516519, compound

Product 1

HCID 226606563-Iodo-4-methoxy-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 2,4-dihydroxy-3-iodopyridine (1.0 eq), Cs2CO3 (2.0 eq), MeI (10.0 eq) and anhydrous DMF was stirred at 40° C. for 72 h, and then the DMF and remaining MeI were evaporated. The residue was treated with aqueous NaS2O3, and the mixture was extracted five times with CH2Cl2. The CH2Cl2 extracts were treated with MgSO4, filtered, and evaporated. The residue was recrystallized from hexanes/CH2Cl2 to give 1-methyl-3-iodo-4-methoxypyridin-2-one.

Workup

  1. customwere evaporated
  2. additionThe residue was treated with aqueous NaS2O3
  3. extractionthe mixture was extracted five times with CH2Cl2
  4. additionThe CH2Cl2 extracts were treated with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was recrystallized from hexanes/CH2Cl2

Sources & evidence

ORD record
ord-5a98d1f395ff43d281d83129ab2b6e90
Source dataset
uspto-grants-2010_06
Patent number
US07745454B2

Reaction notes

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