Hydrochloric Acid → HCID 178524805, compound

HRID 1992130Notes

Reaction equation

HRID 1992130 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][NH:5][N:4]=1.[OH-].[Na+].Cl>C(O)C>[F:14][C:2]([F:1])([F:13])[C:3]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][NH:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178469923HCID 178469923, compound

Product 1

HCID 178524805HCID 178524805, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (100 mg, 0.48 mmol, 1 eq.), ethanol (5 mL) and 5N NaOH (5 mL) was heated to reflux for 72 h. The reaction was cooled to RT, acidified to pH 2 with 5 N HCl and the product extracted into ethyl acetate. The organic layers were dried over sodium sulfate, filtered and concentrated to provide 3-(trifluoromethyl) H-pyrazole-4-carboxylic acid (1a) as a white solid (80 mg, 93% yield). 1H NMR (400 MHz, DMSO-d6) δ 13.95 (broad s, 1H), 8.49 (s, 1H), 3.50 (broad s, 1H). ES-LCMS m/z 181.16 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 72 h
  3. extractionthe product extracted into ethyl acetate
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9b32a9150ff54c5584243826497a4af2
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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