Potassium Carbonate → Ethyl 5-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate

HRID 1731257Notes

Reaction equation

HRID 1731257 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.C(O[CH:15]=[C:16]([C:22]#[N:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:23][C:22]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[N:11]=[CH:15][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 4456866Ethyl 5-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylateYield 28.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Twenty grams of (4-methoxyphenyl)hydrazine hydrochloride, 18.6 g of ethyl (ethoxymethylene)cyanoacetate and 15.2 g of potassium carbonate were combined with 200 ml of ethanol and refluxed for 20 hours. The mixture was cooled and poured into ice water. The precipitated solid was collected by filtration, dried and recrystallized from ethanol to afford 8.1 g of 5-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester. Yield 28%. mp=209°-211° C.

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureThe mixture was cooled
  3. filtrationThe precipitated solid was collected by filtration
  4. customdried
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-84485d1f28834eafaf787837499e4758
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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