Ethanol → 1H-Pyrazole-4-carboxylic acid, 5-(aminocarbonyl)-1-(3,4-dimethylphenyl)-

HRID 867389Notes

Reaction equation

HRID 867389 reaction equation
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=2)[N:6]=[CH:5][C:4]=1[C:16]([O:18]CC)=[O:17])#[N:2].C([OH:23])C.[OH-].[K+]>O>[C:16]([C:4]1[CH:5]=[N:6][N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=2)[C:3]=1[C:1]([NH2:2])=[O:23])([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 13772966HCID 13772966, compound

Product 1

HCID 1637191H-Pyrazole-4-carboxylic acid, 5-(aminocarbonyl)-1-(3,4-dimethylphenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 2.5 g. portion of ethyl 5-cyano-1-(3,4-dimethylphenyl)-4-pyrazolecarboxylate was hydrolysed in 50 ml. of ethanol and 12 ml. of water with 1.3 g. of potassium hydroxide under reflux for 21/4 hours. The mixture was then cooled and poured into 300 ml. of water. The aqueous mixture was filtered, made acid with concentrated hydrochloric acid, and filtered. The solids were dried and recrystallized from ethanol/water to obtain 1.62 g. of the desired product, m.p. 231°-232.5°. Its elemental analysis was as follows:

Workup

  1. temperatureThe mixture was then cooled
  2. additionpoured into 300 ml
  3. filtrationThe aqueous mixture was filtered
  4. filtrationfiltered
  5. customThe solids were dried
  6. customrecrystallized from ethanol/water
  7. customto obtain 1.62 g

Sources & evidence

ORD record
ord-f7db48c5c624470c8f302d77521720ca
Source dataset
uspto-grants-1988_10
Patent number
US04775409

Reaction notes

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