Sodium → methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate

HRID 2351579Notes

Reaction equation

HRID 2351579 reaction equation
[Na].[NH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]([O:11][CH2:12]C)=[O:10])[CH:4]=1>CO>[NH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 14877880ethyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 13324840methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylateYield 74.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 48 mg (2.1 mmol) of sodium in 40 ml of methanol is added 2.0 mg (11.8 mmol) of 5-amino-3-ethoxycarbonyl-1-methylpyrazole, and the mixture is refluxed over night, and distilled under reduced pressure. To the resulting residue are added a small amount of water and sodium chloride, and the mixture is extracted 6 times with chloroform. The extract is dried with magnesium sulfate, chromatographed on a column of silica gel and eluted with ethyl acetate to give 1.37 g (74.1% yield) of the objective compound.

Workup

  1. temperaturethe mixture is refluxed over night
  2. distillationdistilled under reduced pressure
  3. additionTo the resulting residue are added a small amount of water and sodium chloride
  4. extractionthe mixture is extracted 6 times with chloroform
  5. dry with materialThe extract is dried with magnesium sulfate
  6. customchromatographed on a column of silica gel
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-2acea9e5ebbe4025b45c98ee01e9c12d
Source dataset
uspto-grants-1989_10
Patent number
US04873334

Reaction notes

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