Hydrazine, ethyl-, ethanedioate (1:1) → Ethanol

HRID 1787503Notes

Reaction equation

HRID 1787503 reaction equation
[CH2:1]([C:3]1[O:7][N:6]=[C:5]([C:8]([O-:10])=O)[C:4]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C.C(O)(=O)C(O)=O.[CH2:25]([NH:27][NH2:28])[CH3:26]>>[CH2:3]([OH:7])[CH3:1].[CH2:25]([N:27]1[C:8](=[O:10])[C:5]2=[N:6][O:7][CH:3]=[C:4]2[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:28]1)[CH3:26]

Participants

4

Reactant 2

HCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 86614572HCID 86614572, compound

Product 2

HCID 702EthanolYield 1,021.5%HCID 68893536HCID 68893536, compound

Conditions

Temperature
50 °C

Procedure

A mixture of ethylbenzoylisoxazole-3-carboxylate (G. Renzi, V. Dal Piaz et al. Gazz. Chim. Ital., 1968, 98, 656) (0.25 g, 1.02 mmol) and polyphosphoric acid (2.5 g) was gently warmed at 50° C. until the solution became clear. Ethylhydrazine oxalate (0.5 g, 3.33 mmol) was added and the mixture was warmed at 90° C. for 5 hours. After cooling, ice-cold water was added and the precipitate was collected by filtration. The final product was purified by recrystallization from ethanol (0.24 g, 93% yield)

Workup

  1. temperaturethe mixture was warmed at 90° C. for 5 hours
  2. temperatureAfter cooling
  3. additionice-cold water was added
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7449ac2bf4634ef39f7a319a1e903b08
Source dataset
uspto-grants-2009_03
Patent number
US07511038B2

Reaction notes

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