Triethylamine → Ethyl 2-oxopropionate 2,4-dichlorophenylhydrazone

HRID 1872188Notes

Reaction equation

HRID 1872188 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)[C:12]([CH3:14])=[O:13].C(N(CC)CC)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:11]([O:16][CH2:17][CH3:18])[C:12](=[O:13])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12041Ethyl pyruvateHCID 408929(2,4-Dichlorophenyl)hydrazine

Product 1

HCID 69686974Ethyl 2-oxopropionate 2,4-dichlorophenylhydrazoneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-dichlorophenylhydrazine (1.0 g, 4.7 mmol), ethyl pyruvate (0.53 mL, 4.7 mmol), triethylamine (0.65 mL, 4.7 mmol) and ethanol (5 mL) was heated at reflux overnight. The solvent was evaporated and the residue taken up in chloroform. The solution was washed with water and brine and dried over magnesium sulfate and concentrated, leaving an oil (1.1 g, 98%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. washThe solution was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-42ac716bf75f49f795a2988d0612e146
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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