Sodium Hydroxide → 3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)benzoic acid

HRID 1894960Notes

Reaction equation

HRID 1894960 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[C:10]([O:12]C)=[O:11])[CH:4]=[N:3]1.[OH-].[Na+]>CO>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=2)[C:10]([OH:12])=[O:11])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59439420methyl 3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)benzoate

Product 1

HCID 594394183-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)benzoate (Int-5, 22.3 g, 78.5 mmol) in methanol (375 mL), was added 1 N NaOH solution (314 mL, 314 mmol). The reaction was stirred at room temperature for 2 h. The methanol was removed by concentration under reduced pressure and the resulting aqueous mixture was acidified to pH 2 with 1 N HCl. The product was isolated by suction filtration, washed with water and hexane and dried under vacuum to provide 3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)benzoic acid as a white solid (Int-6, 20.3 g, 95.7%). LC-MS: (FA) ES+ 271, ES-269; 1H NMR (400 MHz, d6-DMSO) δ ppm 13.53 (s, 1H), 8.44 (s, 1H), 8.33 (s, 1H), 8.16 (s, 1H), 8.09 (d, J=0.7 Hz, 1H), 7.95 (s, 1H), 3.87 (s, 3H).

Workup

  1. customThe methanol was removed by concentration under reduced pressure
  2. customThe product was isolated by suction filtration
  3. washwashed with water and hexane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f22cd70fe0d74f42b56c7fc6f58acbc7
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

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