Isopropanol → 1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

HRID 1408508Notes

Reaction equation

HRID 1408508 reaction equation
[O:1]1C=CC=[C:2]1[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:17]([F:20])([F:19])[F:18])[CH:7]=1.[O-:21][Mn](=O)(=O)=O.[K+].C(O)(C)C>CC(C)=O>[C:11]1([N:10]2[C:6]([C:2]([OH:1])=[O:21])=[CH:7][C:8]([C:17]([F:20])([F:19])[F:18])=[N:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 516875Potassium PermanganateHCID 57780362HCID 57780362, compound

Product 1

HCID 222503231-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Intermediate 6 (2.84 g, 10.2 mmol) was dissolved in acetone (120 ml) and KMnO4 (11.2 gms, 71.45 mmol in 135 ml water) solution was added to it. This mixture was heated at 60° C. for 3 h and then cooled to rt. Then isopropyl alcohol was added to the reaction mixture and stirred at rt overnight. The reaction mixture filtered through celite and filtrate was evaporated on high vacuum. The residue was dissolved in 1N NaOH and washed with petether. Aqueous layer was acidified with 2N HCl solution to obtain the solid. Solid was filtered and dried on high vacuum to obtain the title compound (2.3 g) as a white solid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.57-7.42 (m, 5H), 7.30 (s, 1H).

Workup

  1. temperaturecooled to rt
  2. filtrationThe reaction mixture filtered through celite and filtrate
  3. customwas evaporated on high vacuum
  4. dissolutionThe residue was dissolved in 1N NaOH
  5. washwashed with petether
  6. customto obtain the solid
  7. filtrationSolid was filtered
  8. customdried on high vacuum

Sources & evidence

ORD record
ord-cb73cdf5523e476ba93034a7169e2afb
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

Loading…