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

HRID 886696Notes

Reaction equation

HRID 886696 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18]([C:20](=[CH:26]OCC)[C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:19]>C(O)C>[NH2:19][C:18]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[N:10]=[CH:26][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 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 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 4-fluorophenylhydrazine hydrochloride (9.76 g, 60 mmol) in ethanol (250 ml) was added triethylamine (9.2 ml, 62 mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10.15 g, 60 mmol). The solution was heated at reflux temperature for 3.5 hours. The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12.1 g) as an off white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux temperature for 3.5 hours
  3. filtrationthe resultant solid was filtered off
  4. washwashed with small amount of ethanol
  5. dry with materialether before being dried under vacuum

Sources & evidence

ORD record
ord-1ad7b471654f4ff58925c10dde93f62b
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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