Methyl iodide → 3-Methoxy-6-methyl-2-nitropyridine

HRID 556507Notes

Reaction equation

HRID 556507 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH3:9][C:10]1[N:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13]([OH:19])=[CH:12][CH:11]=1.C(OC(=O)C)C>CN(C=O)C.O>[CH3:1][O:19][C:13]1[C:14]([N+:16]([O-:18])=[O:17])=[N:15][C:10]([CH3:9])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 848016-Methyl-2-nitropyridin-3-ol

Product 1

HCID 27279653-Methoxy-6-methyl-2-nitropyridineYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (4.15 g) and methyl iodide (2.80 ml) were added to a solution of 6-methyl-2-nitro-3-hydroxypyridine (4.63 g) in DMF (120 ml), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was distributed between ethylacetate and water. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the title compound (3.94 g) as needle crystals.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-790cdb394a3244eea0a64fec920468fa
Source dataset
uspto-grants-2011_11
Patent number
US08058280B2

Reaction notes

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