Methanol → HCID 178498454, compound

HRID 1409386Notes

Reaction equation

HRID 1409386 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[N:2]1.OS(O)(=O)=O.[CH3:14]O>>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:14])=[O:7])=[N:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178524567HCID 178524567, compound

Product 1

HCID 178498454HCID 178498454, compound

Procedure

1H-Pyrazole-3-carboxylic acid (15 g, 133.8 mmol) was dissolved in MeOH (250 ml). Concentrated H2SO4 (30 ml) was added to the solution. The resulting mixture was refluxed for 12 h and concentrated. The residue obtained was quenched by saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic layer was concentrated. Yield 12.05 g. 1H-NMR (400 MHz; CDCl3): δ 3.98 (s, 3H), 6.86 (d, 1H), 7.85 (d, 1H), 11.9 (bs, 1H).

Workup

  1. temperatureThe resulting mixture was refluxed for 12 h
  2. concentrationconcentrated
  3. customThe residue obtained
  4. customwas quenched by saturated aqueous solution of NaHCO3
  5. extractionextracted with EtOAc
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-e9d6f776e2234f7eb0351e4964113b84
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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