Sodium → 2-Methoxy-5-nitropyridine-3-carboxylic acid

HRID 1038453Notes

Reaction equation

HRID 1038453 reaction equation
Cl[C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][O-:15].[Na+].[Na]>CO>[CH3:14][O:15][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 125426642-Chloro-5-nitropyridine-3-carboxylic acid

Product 1

HCID 207150902-Methoxy-5-nitropyridine-3-carboxylic acidYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To 2-chloro-5-nitro-nicotinic acid (1.0 mmol) in methanol was added a solution of sodium methoxide in methanol (2.4 mmol, freshly prepared from sodium metal in methanol). The solution was refluxed for 2 h and the mixture was allowed to cool and concentrated in vacuo. To the resulting residue was added 10% citric acid solution (20 ml) and the solution extracted with ethyl acetate (20 ml). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was crystallised from water to give a yellow-white solid (73%).

Workup

  1. temperatureThe solution was refluxed for 2 h
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. additionTo the resulting residue was added 10% citric acid solution (20 ml)
  5. extractionthe solution extracted with ethyl acetate (20 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallised from water

Sources & evidence

ORD record
ord-488cacb08ca14f5ca7eaf8e7806302ec
Source dataset
uspto-grants-2013_10
Patent number
US08551990B2

Reaction notes

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