Hydrazine hydrate (1:1) → ethyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetate

HRID 570071Notes

Reaction equation

HRID 570071 reaction equation
[C:1]([CH:4]([C:11](=O)[CH3:12])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2].O.[NH2:15][NH2:16]>C(O)C>[CH3:2][C:1]1[C:4]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:11]([CH3:12])[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 87820Ethyl 3-acetyl-4-oxopentanoate

Product 1

HCID 16394806ethyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetateYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 3-acetyl-4-oxopentanoate (synthesized as described D. P. Shrout and D. A. Lightner, Synth. Commun. 20 (1990), 2075) (9.676 g, 51.96 mmol) in ethanol, at 0° C., was added slowly a solution of hydrazine hydrate (2.990 g, 59.75 g) in absolute ethanol. The reaction mixture was warmed to room temperature and stirred for 2 hours. After removing ethanol under vacuum, dichloromethane and water were added to the crude product and the organic layer was separated. The aqueous layer was extracted further with dichloromethane and the combined organic extracts were washed with water. After drying over MgSO4 and evaporation of the solvent under reduced pressure, the pyrazole was isolated as a yellow oil. Yield: 72% (6.777 g, 37.2 mmol).

Workup

  1. customAfter removing ethanol under vacuum, dichloromethane and water
  2. additionwere added to the crude product
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted further with dichloromethane
  5. washthe combined organic extracts were washed with water
  6. dry with materialAfter drying over MgSO4 and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-6a8f0cd3400541e4857ea3b52f549c08
Source dataset
uspto-grants-2015_05
Patent number
US09023315B2

Reaction notes

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