Hydrazine hydrate (1:1) → 4-(1-Hydroxyethyl)pyrazolidin-3-one
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
Product 1
Reagents, catalysts & solvents 1
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
- additionAfter the addition
- customThe resulting reaction mixture
- customwas chromatographed on silica gel (2.2 l)
- washeluting in turn with chloroform
- 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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