Methanol → HCID 178498454, compound

HRID 2194841Notes

Reaction equation

HRID 2194841 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[N:2]1.[CH3:9]O>S(=O)(=O)(O)O>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 178524567HCID 178524567, compound

Product 1

HCID 178498454HCID 178498454, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A 500 mL round-bottomed flask was charged with 1H-pyrazole-3-carboxylic acid 59 (5.0 g, 45 mmol), 100 mL of MeOH, and 10 drops of concentrated sulfuric acid. This mixture was heated to reflux and heating was continued for 12 h. After cooling to room temperature, the solvent was removed and the residue was dissolved in EtOAc and saturated aqueous NaHCO3. The layers were separated and the organic layer was dried and concentrated to give methyl 1H-pyrazole-3-carboxylate 60.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. temperatureheating
  4. customthe solvent was removed
  5. dissolutionthe residue was dissolved in EtOAc
  6. customThe layers were separated
  7. customthe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5655c6744e68420b82f7eadacaa2be7a
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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