Methanol → HCID 178497264, compound

HRID 1188095Notes

Reaction equation

HRID 1188095 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([C:7]2[NH:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=2)=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:21]O>>[C:1]1([CH3:15])[CH:2]=[CH:3][C:4]([C:7]2[NH:11][N:10]=[C:9]([C:12]([O:14][CH3:21])=[O:13])[CH:8]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178423804HCID 178423804, compound

Product 1

HCID 178497264HCID 178497264, compoundYield 84%

Procedure

5-p-Tolyl-1H-pyrazole-3-carboxylic acid (250 mg, 1.24 mmol) and sulfuric acid (120 μL, 1.48 mmol) in methanol (5 mL) were heated to reflux for 16 hrs. The solvent was evaporated and the residue was resuspended in CH2Cl2. The residue was filtrated and the filtrate was washed with water and brine and dried over Na2SO4. Solvent was evaporated and the white solid was combined with the precipitate collected previously. Methyl 5-p-tolyl-1H-pyrazole-3-carboxylate (224 mg, 84%) was obtained as a white solid. 1H-NMR (400 MHz, CDCl3): (ppm)=7.56 (d, J=7.6 Hz, 2H), 7.22 (d, J=8.0 Hz, 2H), 7.02 (s, 1H), 3.91 (s, 3H), 2.36 (s, 3H).

Workup

  1. temperatureto reflux for 16 hrs
  2. customThe solvent was evaporated
  3. filtrationThe residue was filtrated
  4. washthe filtrate was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customSolvent was evaporated
  7. customcollected previously

Sources & evidence

ORD record
ord-f1739a3bb10b4db8971d476476d82697
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

Loading…