Methyl iodide → 1-methyl-5-nitro-2(1H)-pyridinone

HRID 1441730Notes

Reaction equation

HRID 1441730 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:11][N:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178526703HCID 178526703, compound

Product 1

HCID 2958661-methyl-5-nitro-2(1H)-pyridinoneYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-5-nitropyridine (600 mg, 4.28 mmol, 1 eq) in DMF (5 mL) was added cesium carbonate (1.67 g, 5.16 mmol, 1.2 eq), followed by methyl iodide (0.4 mL, 6.42 mmol, 1.5 eq). After stirring overnight, the reaction mixture was quenched with water and extracted with ethyl ether (5×20 mL). The ether was dried over Na2SO4 and concentrated under reduced pressure. The crude material was column chromatographed, eluting with 50% EtOAc/hexanes to give 450 mg of compound 50B.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl ether (5×20 mL)
  3. dry with materialThe ether was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed
  6. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-f82daeb7c53a4ba483d3c5949a3d4adb
Source dataset
uspto-grants-2010_02
Patent number
US07655688B2

Reaction notes

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