Hydrazine hydrate (1:1) → HCID 53629156, compound

HRID 1896362Notes

Reaction equation

HRID 1896362 reaction equation
O.[NH2:2][NH2:3].N[O:5][C:6](=O)[CH2:7][N:8]1[CH2:12][CH:11]([CH2:13][CH2:14][CH3:15])[CH2:10][C:9]1=[O:16]>CCO.[Cl-].[Na+].O>[O:16]=[C:9]1[CH2:10][CH:11]([CH2:13][CH2:14][CH3:15])[CH2:12][N:8]1[CH2:7][C:6]([NH:2][NH2:3])=[O:5]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53629155HCID 53629155, compound

Product 1

HCID 53629156HCID 53629156, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In a 250 ml three necked flask fitted with a magnetic stirrer, hydrazine hydrate (5.78 g, 0.18 mol, 3 eq) is added to a solution of 1-[2-(aminooxy)-2-oxoethyl]-4-propylpyrrolidin-2-one x40 (11.99 g, 60.29 mmol) in EtOH (125 ml). The mixture is heated 4 h at reflux, cooled down to room temperature, diluted with brine and extracted with CH2Cl2. The combined organic phases are dried over MgSO4, filtered and evaporated to afford 11.0 g of 2-(2-oxo-4-propylpyrrolidin-1-yl)acetohydrazide x41.

Workup

  1. temperatureThe mixture is heated 4 h
  2. temperatureat reflux
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e04da80cfcbe43879df662a15c872c59
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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