Sodium Hydroxide → HCID 59739552, compound

HRID 1192958Notes

Reaction equation

HRID 1192958 reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][N:8]([CH3:15])[N:7]=1)=[O:5])C.[OH-].[Na+]>CO>[CH3:15][N:8]1[CH:9]=[C:10]([C:11]([F:13])([F:14])[F:12])[C:6]([C:4]([OH:5])=[O:3])=[N:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57574534HCID 57574534, compound

Product 1

HCID 59739552HCID 59739552, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-Methyl-4-trifluoromethyl-1H-pyrazole-3-carboxylic acid ethyl ester (20 g, 90 mmol) was dissolved in methanol (100 ml). Sodium hydroxide in methanol (1M) (95 ml, 95 mmol) was added dropwise. The mixture was stirred at room temperature for 2 hours, stored at room temperature for 16 hours and concentrated. The residue was dissolved in aqueous hydrochloric acid (2M) (55 ml) and isopropyl acetate (300 ml). The two phases were separated and the aqueous phase was extracted with more isopropyl acetate (100 ml). The combined organic extracts were dried over magnesium sulfate and concentrated. This gave the product as a white solid (17.5 g, 100% yield). M.p. 174-175° C.

Workup

  1. waitstored at room temperature for 16 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in aqueous hydrochloric acid (2M) (55 ml)
  4. customThe two phases were separated
  5. extractionthe aqueous phase was extracted with more isopropyl acetate (100 ml)
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-10bb3bd29a7f423894ada258a73bbca2
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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