Hydrazine hydrate (1:1) → 4-(1-Hydroxyethyl)pyrazolidin-3-one

HRID 1029668Notes

Reaction equation

HRID 1029668 reaction equation
O.[NH2:2][NH2:3].[OH:4][CH:5]([C:7](=[CH2:13])[C:8](OCC)=[O:9])[CH3:6]>C(O)C>[OH:4][CH:5]([CH:7]1[CH2:13][NH:3][NH:2][C:8]1=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10855587Butanoic acid, 3-hydroxy-2-methylene-, ethyl ester

Product 1

HCID 143142834-(1-Hydroxyethyl)pyrazolidin-3-oneYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To hydrazine hydrate (38.6 g) was added dropwise a solution of ethyl 2-(1-hydroxyethyl)acrylate (106 g) in ethanol (20 ml) at 0° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 4 hours at the same temperature. The resulting reaction mixture was chromatographed on silica gel (2.2 l) eluting in turn with chloroform and a mixture of chloroform and methanol (8:1→2:1→1:1, V/V) to give 4-(1-hydroxyethyl)-3-pyrazolidinone (68 g).

Workup

  1. additionAfter the addition
  2. customThe resulting reaction mixture
  3. customwas chromatographed on silica gel (2.2 l)
  4. washeluting in turn with chloroform
  5. additiona mixture of chloroform and methanol (8:1→2:1→1:1, V/V)

Sources & evidence

ORD record
ord-f1171f2b3ef34aa3a0358caba1e01006
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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