Diethyl Oxalate → Ethyl 2-hydrazinyl-2-oxoacetate

HRID 2175411Notes

Reaction equation

HRID 2175411 reaction equation
[C:1]([O:8]CC)(=O)[C:2]([O:4][CH2:5][CH3:6])=[O:3].O.[NH2:12][NH2:13]>>[NH:12]([C:1](=[O:8])[C:2]([O:4][CH2:5][CH3:6])=[O:3])[NH2:13]

Participants

3

Reactant 2

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

Product 1

HCID 2786935Ethyl 2-hydrazinyl-2-oxoacetateYield 55.3%

Procedure

To a solution of diethyl oxalate (9-1) (6.0 g, 41.04 mmol) in alcohol (30 mL) was added hydrazine hydrate (2.4 mL, 49.26 mmol) dropwise at −20° C. After the addition was over, the solution was stirred for 30 min. The solution was filtered and the filtrate was evaporated to give the product as a white solid (3.0 g, 55%). The compound was used for the next step directly without further purification. LRMS (ESI) calculated M+H for C4H9N2O3: 133.1. Found: 133.3.

Workup

  1. additionAfter the addition
  2. filtrationThe solution was filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-cc7019a1ee74480e8f2ec9e7065bd4e7
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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