Methyl iodide → 3-Methoxy-4-methyl-2-nitropyridine

HRID 1828528Notes

Reaction equation

HRID 1828528 reaction equation
[OH:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[C:12](=O)([O-])[O-].[Cs+].[Cs+].CI.C(OCC)(=O)C>CN(C)C=O.CCCCCC>[CH3:12][O:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 139002304-Methyl-2-nitropyridin-3-ol

Product 1

HCID 149295773-Methoxy-4-methyl-2-nitropyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

3-Hydroxy-4-methyl-2-nitropyridine (5 g) was dissolved in dimethylformamide (50 ml), added with cesium carbonate (11.6 g) and methyl iodide (13.7 g), and then the mixture was stirred overnight at room temperature. The reaction mixture was added with ethyl acetate and hexane, washed with water and dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain the title compound (quantitative).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d8b863c73e0e4ca18bc54436aa86d8dd
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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