Sodium Hydroxide → 5-Amino-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

HRID 1978167Notes

Reaction equation

HRID 1978167 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]([O:14]CC)=[O:13].[OH-].[Na+]>O>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9837602Ethyl 5-amino-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 101305025-Amino-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 10 ml of water, 2.37 g (10 mmol) of ethyl 5-amino-1-methyl-3-trifluoromethylpyrazole-4-carboxylate and 0.44 g (11 mmol) of sodium hydroxide were added and stirred at 60° C. for 10 hours. After cooling to room temperature, the reaction mixture was washed with toluene. The resulting aqueous solution was made pH 1 by adding concentrated hydrochloric acid. Precipitate was filtered and dried to obtain 1.78 g of desired 5-amino-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid as white solid. The yield was 85% Following results were obtained by NMR analysis.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe reaction mixture was washed with toluene
  3. additionby adding concentrated hydrochloric acid
  4. filtrationPrecipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-f8f3dbff06d54d1c8943fb2727e273d8
Source dataset
uspto-grants-2001_05
Patent number
US06235911B1

Reaction notes

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