Ethyl Acetoacetate → 1-(3,4-Dimethylphenyl)-3-methyl-3-pyrazolin-5-one

HRID 2085356Notes

Reaction equation

HRID 2085356 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][NH2:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:11](OCC)(=[O:16])[CH2:12][C:13]([CH3:15])=O>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:11](=[O:16])[CH:12]=[C:13]([CH3:15])[NH:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 1737411-(3,4-Dimethylphenyl)hydrazine

Product 1

HCID 117358291-(3,4-Dimethylphenyl)-3-methyl-3-pyrazolin-5-oneYield 156.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,4-dimethylphenylhydrazine (7.3 g; 0.053 mol.) and ethyl acetoacetate (6.9 g; 0.053 mol.) in glacial acetic acid (50.0 mL) was stirred and heated at 100° for 24 h. The solvent was evaporated and the product purified by chromatography (silica gel, 50% ethyl acetate/hexanes) to afford the title compound (16.8 g; 64%). MS(ES) m/z 203 [M+H].

Workup

  1. temperatureheated at 100° for 24 h
  2. customThe solvent was evaporated
  3. customthe product purified by chromatography (silica gel, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-10e7b5e7ebe84c43a488d0cfbc89fb57
Source dataset
uspto-grants-2004_04
Patent number
US06720345B1

Reaction notes

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