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

HRID 53528

Reaction equation

HRID 53528 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-3d639581d26c44ddb7f10dbba34ccf92
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Linked notes

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