Hydrochloric Acid → HCID 13882132, compound

HRID 867380Notes

Reaction equation

HRID 867380 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[Cl:8].[OH-:21].[K+].Cl>C(O)C>[C:16]([C:12]1[CH:11]=[N:10][N:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[C:13]=1[C:14]([NH2:15])=[O:21])([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13654088HCID 13654088, compound

Product 1

HCID 13882132HCID 13882132, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Fifteen g. of ethyl 1-(3,4-dichlorophenyl)-5-cyano-4-pyrazolecarboxylate was dissolved in 200 ml. of ethanol, and 5.6 g. of potassium hydroxide wasadded. The reaction mixture was stirred under reflux for 1 hour, and was then poured over a large amount of ice and made acid with concentrated hydrochloric acid. The mixture was filtered, and the solids were found by nuclear magnetic resonance analysis to consist of the partially hydrolyzed4-carboxy-5-cyanopyrazole. A 2 g. portion of that intermediate was held outfor further examination, and the rest of the solids were redissolved in 200ml. of ethanol and stirred under reflux for 18 hours with 5.6 g. of potassium hydroxide. The mixture was then poured over ice, made acid, and filtered. The solids were recrystallized from ethanol, and the mother liquor was chromatographed over a silica gel column with methanol as the eluent. The product-containing fractions were evaporated to dryness and the residues were recrystallized from methanol to obtain the desired product, m.p. 249°-250°. The elemental analysis was as follows.

Workup

  1. temperatureunder reflux for 1 hour
  2. additionwas then poured over a large amount of ice
  3. filtrationThe mixture was filtered
  4. dissolutionthe rest of the solids were redissolved in 200ml
  5. stirringof ethanol and stirred
  6. temperatureunder reflux for 18 hours with 5.6 g
  7. additionThe mixture was then poured over ice
  8. filtrationfiltered
  9. customThe solids were recrystallized from ethanol
  10. customthe mother liquor was chromatographed over a silica gel column with methanol as the eluent
  11. customThe product-containing fractions were evaporated to dryness
  12. customthe residues were recrystallized from methanol

Sources & evidence

ORD record
ord-8c5b9279f3294456837c93f7ab07d226
Source dataset
uspto-grants-1988_10
Patent number
US04775409

Reaction notes

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