Methanol → HCID 178498454, compound

HRID 1912460Notes

Reaction equation

HRID 1912460 reaction equation
S(=O)(=O)(O)O.[NH:6]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[N:7]1.[CH3:14]O>>[CH3:14][O:12][C:11]([C:8]1[CH:9]=[CH:10][NH:6][N:7]=1)=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178524567HCID 178524567, compound

Product 1

HCID 178498454HCID 178498454, compoundYield 62%

Procedure

Sulfuric acid (5.8 mL) was added dropwise to a stirred solution of 1H-pyrazole-3-carboxylic acid (1 g, 8.92 mmol) in MeOH (65 mL) at 0° C. After the addition was completed the mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was concentrated in vacuo and the residue was dissolved in water and basified with NaHCO3 (aq. sat. solution). The mixture was extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo to yield 1H-pyrazole-3-carboxylic acid methyl ester (0.7 g, 62% yield) as a white solid which was used in the next step without further purification.

Workup

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in water
  4. extractionThe mixture was extracted with AcOEt
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-1f5252abced24a56b138a200294a6187
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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