Potassium Carbonate → Ethyl 5-amino-1-(3-chlorophenyl)-1H-pyrazole-4-carboxylate

HRID 1731260Notes

Reaction equation

HRID 1731260 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH2:11]([O:13][C:14](=[O:22])[C:15](=[CH:18]OCC)[C:16]#[N:17])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:17][C:16]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=2)[N:10]=[CH:18][C:15]=1[C:14]([O:13][CH2:11][CH3:12])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 757292Ethyl 5-amino-1-(3-chlorophenyl)-1H-pyrazole-4-carboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 53.7 g of (3-chlorophenyl)hydrazine hydrochloride, 50.8 g of ethyl(ethoxymethylene)cyanoacetate and 41.4 g of potassium carbonate in 500 ml of ethanol was refluxed for 20 hours. The solution was poured into ice water. The precipitated solid was collected by filtration, dried and recrystallized from ethanol/water to provide 53.0 g of 5-amino-1-(3-chlorophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester. Yield 67%. mp=115°-117° C.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customdried
  3. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-92765eba177d4875b6ce732748c3c743
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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