Potassium Hydroxide → 1H-Pyrazole-4-carboxylic acid, 5-(aminocarbonyl)-1-(4-methylphenyl)-

HRID 867381Notes

Reaction equation

HRID 867381 reaction equation
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[C:15]([O:17]CC)=[O:16])#[N:2].[OH-:20].[K+]>O>[C:15]([C:4]1[CH:5]=[N:6][N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:1]([NH2:2])=[O:20])([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13772970Ethyl 5-cyano-1-(4-methylphenyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 1637161H-Pyrazole-4-carboxylic acid, 5-(aminocarbonyl)-1-(4-methylphenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 10 g. of ethyl 5-cyano-1-(4-methylphenyl)-4-pyrazolecarboxylate was added 5.6 g. of potassium hydroxide and 200 ml. of water followed by enough water to cause solution. The mixture was stirred under reflux for 8hours and allowed to stand for 3 days. It was then poured over ice, made acid and filtered. The solids from the filtration were heated in 100 ml. of ethyl acetate, and the undissolved solid was separated, dried and identified as 4.25 g. of the desired product, m.p. 260° dec. The product was identified by nuclear magnetic resonance analysis in DMSOd6. δ2.36 (s, 3), methyl; 7.32 (d, 2), aromatic; 7.45 (d, 2), aromatic; 8.01 (s, 1), pyrazole; 7.91 (s, 1), carboxamide; 8.33 (s, 1), carboxamide.

Workup

  1. temperatureunder reflux for 8hours
  2. additionIt was then poured over ice
  3. filtrationfiltered
  4. filtrationThe solids from the filtration
  5. temperaturewere heated in 100 ml
  6. customof ethyl acetate, and the undissolved solid was separated
  7. customdried

Sources & evidence

ORD record
ord-5868a1ee510c42739b17dc774485354b
Source dataset
uspto-grants-1988_10
Patent number
US04775409

Reaction notes

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