Water → ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

HRID 973697Notes

Reaction equation

HRID 973697 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(O[CH:14]=[C:15]([C:21]#[N:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[CH2:19]([O:18][C:16]([C:15]1[CH:14]=[N:10][N:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[C:21]=1[NH2:22])=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 688689ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 11.38 g (70.0 mmole) of a commercially available sample of 4-fluorophenylhydrazine hydrochloride, 11.84 g (70.0 mmole) of ethyl (ethoxymethylene)cyanoacetate and 9.67 g (70.0 mmole) of potassium carbonate in 100 ml of ethanol was refluxed overnight and then treated with 300 ml of water. The precipitate was filtered and dried in vacuo to furnish 12.87 g (74% yield) of pale yellow crystalline solid. The sample was recrystallized from ethanol m.p. 151-2° C.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe precipitate was filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-f4f4fdc6111e4d59bd670b2040729ad3
Source dataset
uspto-grants-1991_11
Patent number
US05064851

Reaction notes

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