Water → HCID 13882136, compound

HRID 978948Notes

Reaction equation

HRID 978948 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([C:14]#[N:15])=[C:12]([C:16]([O:18]CC)=[O:17])[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].[OH-:21].[K+].O>C(O)C.C(O)(=O)C>[C:16]([C:12]1[CH:11]=[N:10][N:9]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([Cl:1])[CH:3]=2)[C:13]=1[C:14]([NH2:15])=[O:21])([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium Hydroxide2×HCID 13772964HCID 13772964, compound

Product 1

HCID 13882136HCID 13882136, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

A 9.5 g. portion of ethyl 1-(3-chloro-4-methylphenyl)-5-cyano-4-pyrazolecarboxylate was dissolved in 250 ml. of ethanol, and 2 g. of potassium hydroxide was added. The mixture was then stirred under reflux for 30 minutes. One hundred ml. of water was added, and the mixture was stirred under reflux for an additional 4 hours. Isolation of the product was attempted, but it was found to be a difficultly separable mixture, and the entire reaction mixture was returned to the flask, redissolved in aqueous ethanol and refluxed for 1 hour on the steam bath with 6 g. of additional potassium hydroxide. The mixture was then diluted with aqueous acetic acid and filtered, and the solids were dried and identified as 5.2 g. of the desired product, m.p. 228°-232° dec. It was identified by elemental analysis.

Workup

  1. temperatureunder reflux for 30 minutes
  2. stirringthe mixture was stirred
  3. temperatureunder reflux for an additional 4 hours
  4. customthe entire reaction mixture
  5. temperaturerefluxed for 1 hour on the steam bath with 6 g
  6. filtrationfiltered
  7. customthe solids were dried

Sources & evidence

ORD record
ord-02e97188a76c4f23b87ecb54346e15ca
Source dataset
uspto-grants-1987_05
Patent number
US04666504

Reaction notes

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