Hydrazine hydrate (1:1) → 3,5-diethyl-1H-pyrazole

HRID 2043749Notes

Reaction equation

HRID 2043749 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH2:4][C:5](=O)[CH2:6][CH3:7].O.[NH2:11][NH2:12]>C(O)(=O)C.O>[CH2:2]([C:3]1[CH:4]=[C:5]([CH2:6][CH3:7])[NH:12][N:11]=1)[CH3:1]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 819233,5-Heptanedione

Product 1

HCID 43063673,5-diethyl-1H-pyrazoleYield 91.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

A solution of 3,5-heptanedione (2.4 g, 18.8 mmol) and hydrazine hydrate (1.0 g, 19.0 mmol) and acetic acid (1 drop) in water (10 mL) was heated to reflux for 1 h. The reaction mixture was then cooled in an ice bath to form a white precipitate. The precipitate was then filtered, dissolved in chloroform and dried over MgSO4. The resulting reaction was concentrated under reduced pressure to provide 2.14 g of the title compound. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. temperatureto reflux for 1 h
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. customto form a white precipitate
  4. filtrationThe precipitate was then filtered
  5. dissolutiondissolved in chloroform
  6. dry with materialdried over MgSO4
  7. customThe resulting reaction
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-f4f1b0f13c8f4246901054cb4ec64009
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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