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

HRID 1814203Notes

Reaction equation

HRID 1814203 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([NH:10][NH2:11])[CH:6]=[CH:7][C:8]=1[CH3:9].[C:12](OCC)(=[O:17])[CH2:13][C:14]([CH3:16])=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:2][C:3]1[CH:4]=[C:5]([N:10]2[C:12](=[O:17])[CH:13]=[C:14]([CH3:16])[NH:11]2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 1737401-(3,4-Dimethylphenyl)hydrazine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 117358291-(3,4-Dimethylphenyl)-3-methyl-3-pyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,4-dimethylphenylhydrazine hydrochloride (17.7 g; 0.1 mol.), ethyl acetoacetate (13.0 g; 0.1 mol.) and sodium acetate (8.2 g; 0.1 mol.) in glacial acetic acid (250 mL) was stirred and heated under reflux for 24 h.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 h.

Sources & evidence

ORD record
ord-564b5a3f96434e96afde9c1bfc31a5fa
Source dataset
uspto-grants-2005_04
Patent number
US06875786B2

Reaction notes

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