Hydrazine → Ethyl (5-oxo-2,5-dihydro-1H-pyrazol-3-yl)acetate

HRID 606520Notes

Reaction equation

HRID 606520 reaction equation
O=[C:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][C:4](OCC)=[O:5].[NH2:15][NH2:16]>CCO>[O:5]=[C:4]1[NH:16][NH:15][C:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66045Diethyl acetonedicarboxylate

Product 1

HCID 43831447Ethyl (5-oxo-2,5-dihydro-1H-pyrazol-3-yl)acetateYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of diethyl 3-oxopentanedioate (26.0 g, 129 mmol) in EtOH (250 mL) was added hydrazine (4.38 g, 129 mmol) at room temperature, and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from diethyl ether-hexane to give the title compound as a white powder (9.79 g, 45%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-9afd592fc70c4c1188bf37f1705bcb17
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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