Methanol → methyl 1-methyl-1H-pyrazole-3-carboxylate

HRID 530811Notes

Reaction equation

HRID 530811 reaction equation
[C:1](=[O:4])([OH:3])N.[N:5]1[N:9]2[CH:10]=CC=C[C:8]2=[C:7](C(OC)=O)[CH:6]=1.S(=O)(=O)(O)O.[CH3:23]O>>[CH3:10][N:9]1[CH:8]=[CH:7][C:6]([C:1]([O:3][CH3:23])=[O:4])=[N:5]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 90419258Methyl pyrazolo[1,5-a]pyridine-3-carboxylate carbamate

Product 1

HCID 7017175methyl 1-methyl-1H-pyrazole-3-carboxylate

Procedure

To a solution of compound 1 (1.26 g, 10 mmol) in methanol (30 mL) was added sulfuric acid (0.5 mL). The resulting mixture was refluxed for 2 h and the solvent was evaporated. The residue was dissolved in EA (60 mL) and washed with brine, dried over Na2SO4. Then filtered and concentrated to give the product.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in EA (60 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationThen filtered
  7. concentrationconcentrated
  8. customto give the product

Sources & evidence

ORD record
ord-f3dbd1453946429894a2b8a33962d031
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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