Water → HCID 13882136, compound

HRID 867386Notes

Reaction equation

HRID 867386 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 in250 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 wasadded, 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-98c204bc25e74657a22f2b80334a87cd
Source dataset
uspto-grants-1988_10
Patent number
US04775409

Reaction notes

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