Methanol → Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

HRID 1045960Notes

Reaction equation

HRID 1045960 reaction equation
OS(O)(=O)=O.[CH3:6][N:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([C:15]([OH:17])=[O:16])=[N:8]1.[CH3:18]O>>[CH3:6][N:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([C:15]([O:17][CH3:18])=[O:16])=[N:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5359761-Methyl-4-nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 54775322Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

Procedure

Concentrated H2SO4 (0.4 ml) was added to 1-methyl-4-nitropyrazole-3-carboxylic acid (2.02 g) in MeOH (40 ml) and the mixture heated to reflux for 4 hours. After cooling to room temperature, the reaction was concentrated in vacuo. The crude material was dissolved in EtOAc (60 ml) then washed with water (10 ml) and brine (10 ml). The organic layer was dried, filtered and concentrated to give methyl 1-methyl-4-nitropyrazole-3-carboxylate, 1.96 g.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 hours
  3. concentrationthe reaction was concentrated in vacuo
  4. dissolutionThe crude material was dissolved in EtOAc (60 ml)
  5. washthen washed with water (10 ml) and brine (10 ml)
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-85a4d9ac26f1445ea89bdae70329acb6
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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