Ethyl 4,4,4-trifluoroacetoacetate → 3H-Pyrazol-3-one, 2,4-dihydro-2,5-diphenyl-

HRID 1289883Notes

Reaction equation

HRID 1289883 reaction equation
F[C:2](F)(F)[C:3](=O)[CH2:4][C:5]([O:7]CC)=O.Cl.Cl[C:15]1[CH:16]=[C:17]([NH:21][NH2:22])[CH:18]=[CH:19][CH:20]=1>C(O)(=O)C>[C:17]1([N:21]2[C:5](=[O:7])[CH2:4][C:3]([C:2]3[CH:17]=[CH:16][CH:15]=[CH:20][CH:19]=3)=[N:22]2)[CH:18]=[CH:19][CH:20]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 75331m-Chlorophenylhydrazine hydrochloride

Product 1

HCID 785593H-Pyrazol-3-one, 2,4-dihydro-2,5-diphenyl-Yield 96.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl trifluoroacetoacetate (5 g, 27.2 mmol), 3-chlorophenylhydrazine hydrochloride (4.86 g, 27.2 mmol) and acetic acid (50 mL) was heated at 100° C. overnight. The reaction mixture was concentrated in vacuo, CH2Cl2 (80 mL) and hexane (40 mL) were added to the residue and the solid which formed was collected by filtration to afford 3.11 g of 2,4-dihydro-2-(3-chlorophenyl)-5-trifluoromethyl-3H-pyrazol-3-one (Formula III: R1 =3-Cl--Ph; R2 =CF3 ; R3 =H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, CH2Cl2 (80 mL) and hexane (40 mL)
  2. additionwere added to the residue
  3. customthe solid which formed
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-8f70a0e131ff4c60b92e9ce4d8ea848b
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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