Methanol → Methyl 1-isopropyl-1H-pyrazole-3-carboxylate

HRID 1526602Notes

Reaction equation

HRID 1526602 reaction equation
[CH:1]([N:4]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[N:5]1)([CH3:3])[CH3:2].S(=O)(=O)(O)O.[CH3:17]O>>[CH:1]([N:4]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:17])=[O:10])=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 196198851-(Propan-2-yl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 19576723Methyl 1-isopropyl-1H-pyrazole-3-carboxylateYield 76%

Procedure

To a solution of 1-isopropyl-1 h-pyrazole-3-caboxylic acid (0.9757 g, 6.33 mmol, Matrix Scientific) in MeOH (31.6 ml) in a glass pressure vessel was added sulfuric acid (0.355 ml, 6.33 mmol Sigma Aldrich). The vessel was sealed and the rxn was brought to reflux to stir. (NOTE: A portable blast shield was used.) Rxn was allowed to stir for 5 hours. The rxn was concentrated in vacuo. The residue was diluted with water and extracted with EtOAc. The organic extract was washed with water, dried over MgSO4, filtered and concentrated in vacuo to give methyl 1-isopropyl-1H-pyrazole-3-carboxylate (0.8073 g, 4.80 mmol, 76% yield) as a clear oil. MS m/z=168.9 [M+H]+. Calculated for C8H12N2O2: 168.09. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.55 (d, J=6.85 Hz, 6H) 3.93 (s, 3H) 4.63 (dt, J=13.50, 6.75 Hz, 1H) 6.83 (d, J=2.35 Hz, 1H) 7.46 (d, J=2.35 Hz, 1H)

Workup

  1. customThe vessel was sealed
  2. temperatureto reflux to stir
  3. concentrationThe rxn was concentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5436364b504543719961eb3d9e3b4cad
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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