Diethyl Oxalate → Ethyl 2-hydrazinyl-2-oxoacetate

HRID 541252

Reaction equation

HRID 541252 reaction equation
[C:1]([O:8]CC)(=O)[C:2]([O:4][CH2:5][CH3:6])=[O:3].O.[NH2:12][NH2:13]>C(O)C>[NH:12]([C:1](=[O:8])[C:2]([O:4][CH2:5][CH3:6])=[O:3])[NH2:13]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 2786935Ethyl 2-hydrazinyl-2-oxoacetateYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a round-bottom flask was added a solution of diethyl oxalate (10.0 g, 68.4 mmol, 1.00 equiv) in ethanol (100 mL). Hydrazine hydrate (2.75 g, 85.8 mmol, 1.00 equiv) was added and the resulting mixture was stirred for 3 h at 80° C. After cooling to ambient temperature, the solids were removed via filtration and the filtrate was concentrated in vacuo to yield 8.00 g (80%) of the title compound as a colorless oil.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe solids were removed via filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9d12edd2be484311be42d75512ec3b4e
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Linked notes

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