Sodium Hydroxide → HCID 59516080, compound

HRID 1160561Notes

Reaction equation

HRID 1160561 reaction equation
[OH-].[Na+].[C:3]([C:7]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)[N:10]=[CH:9][C:8]=1[C:23]([O:25]CC)=[O:24])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([C:7]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:20])([F:22])[F:21])[CH:13]=2)[N:10]=[CH:9][C:8]=1[C:23]([OH:25])=[O:24])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59516093HCID 59516093, compound

Product 1

HCID 59516080HCID 59516080, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of Sodium hydroxide (6.67 mL, 13.34 mmol) was added in one portion to a stirred solution of ethyl 5-tert-butyl-1-(4-chloro-3-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylate (Intermediate#120) (1 g, 2.67 mmol) in methanol (20 mL). The resulting suspension was stirred at 80° C. for 6 hours. The resulting mixture was evaporated to remove the methanol, washed with ether (20 mL). The reaction mixture was acidified with 2M HCl, extracted with ethyl acetate(2×30 mL) The organic layers were combined and washed with water (10 mL) and brine (10 mL), dried over MgSO4, filtered and evaporated to afford pure 5-tert-butyl-1-(4-chloro-3-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylic acid (0.766 g, 83%).

Workup

  1. customThe resulting mixture was evaporated
  2. customto remove the methanol
  3. washwashed with ether (20 mL)
  4. extractionextracted with ethyl acetate(2×30 mL) The organic layers
  5. washwashed with water (10 mL) and brine (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4aae567bf84140728baa628f2002937c
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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