Water → 2-Methoxy-4-methyl-5-nitropyridine

HRID 2380243Notes

Reaction equation

HRID 2380243 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][N:6]=1.O>CO>[CH3:1][O:2][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 2431692-Methoxy-4-methyl-5-nitropyridineYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (26.1 g) was added to a solution of 2-chloro-4-methyl-5-nitropyridine (19.0 g) in methanol (100 ml) and the resulting mixture was refluxed for 12 hours. Upon cooling, the mixture was poured over water (1 L), and the product was extracted with ethyl acetate and washed with water. The organic phase was dried (anhydrous magnesium sulfate) and concentrated, and the residue dissolved in hot ether and filtered. Crystallization from ether provided 10.2 g of the title compound, suitable for use in the next reaction.

Workup

  1. temperaturethe resulting mixture was refluxed for 12 hours
  2. temperatureUpon cooling
  3. extractionthe product was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  6. concentrationconcentrated
  7. dissolutionthe residue dissolved in hot ether
  8. filtrationfiltered
  9. customCrystallization from ether

Sources & evidence

ORD record
ord-2710462d174b48a38fd8d9e30632869f
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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