Acetic Acid → Ethyl pyruvate 2,4-dichlorophenylhydrazone

HRID 50032

Reaction equation

HRID 50032 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][NH2:10].[C:11]([O:16][CH2:17][CH3:18])(=[O:15])[C:12]([CH3:14])=O.C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][N:10]=[C:12]([CH3:14])[C:11]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12041Ethyl pyruvateHCID 408929(2,4-Dichlorophenyl)hydrazine

Product 1

HCID 85437209Ethyl pyruvate 2,4-dichlorophenylhydrazoneYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-dichlorophenylhydrazine (16.00 g, 0.075 mol), ethyl pyruvate (14.47 g, 10.3 mL, 0.12 mol), glacial acetic acid (0.9 mL), absolute ethanol (105 mL) was refluxed for 2 hours. After cooling at room temperature, the solid which formed was filtered and recrystallized from ethanol to give 17.0 g (83%) of the title compound, mp 118-120° C. (from ethanol).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe solid which formed
  3. filtrationwas filtered
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cbbfad43ce4a4efb9b67fb7c1f55dfcc
Source dataset
uspto-grants-2004_03
Patent number
US06710068B2

Linked notes

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