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

HRID 867383Notes

Reaction equation

HRID 867383 reaction equation
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:6]=[CH:5][C:4]=1[C:15]([O:17]CC)=[O:16])#[N:2].C([OH:22])C.[OH-].[K+]>O>[C:15]([C:4]1[CH:5]=[N:6][N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[C:3]=1[C:1]([NH2:2])=[O:22])([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 1636721H-Pyrazole-4-carboxylic acid, 5-cyano-1-(3-methylphenyl)-, ethyl ester

Product 1

HCID 1637171H-Pyrazole-4-carboxylic acid, 5-(aminocarbonyl)-1-(3-methylphenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 9 g. portion of ethyl 5-cyano-1-(3-methylphenyl)-4-pyrazolecarboxylate was dissolved in 200 ml. of ethanol, and 5.8 g. of potassium hydroxide wasadded. The mixture was stirred under reflux for 4 hours, and then was cooled, diluted with water and made acid. The mixture was filtered, and the solids were washed with ethyl acetate as shown above in Example 8 to obtain 3.8 g. of the desired product, m.p. 209°-211° dec. Itwas identified by elemental analysis.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturewas cooled
  3. filtrationThe mixture was filtered
  4. washthe solids were washed with ethyl acetate
  5. customto obtain 3.8 g

Sources & evidence

ORD record
ord-c5a75c98e24546d3ad58e622fd924d55
Source dataset
uspto-grants-1988_10
Patent number
US04775409

Reaction notes

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