Glyoxal → 1-(1-ethyl-4-hydroxy-1H-pyrazol-3-yl)ethanone

HRID 1880331Notes

Reaction equation

HRID 1880331 reaction equation
[CH:1]([CH:3]=O)=[O:2].[CH2:5]([NH:7][N:8]=[CH:9][C:10](=[O:12])[CH3:11])[CH3:6]>O>[CH2:5]([N:7]1[CH:11]=[C:10]([OH:12])[C:9]([C:1](=[O:2])[CH3:3])=[N:8]1)[CH3:6]

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 860145522-Oxopropanal ethylhydrazone

Product 1

HCID 669205971-(1-ethyl-4-hydroxy-1H-pyrazol-3-yl)ethanoneYield 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 40% aqueous solution of glyoxal (2.3 g, 1.8 mL, 16 mmol) was added to a solution of 2-oxopropanal ethylhydrazone (1.83 g, 16 mmol) in water (90 mL). The mixture was heated at reflux for 1 hour. The reaction was cooled to room temperature and extracted with CH2Cl2 (4×). The combined organic extracts were dried over Na2SO4, filtered and concentrated to afford 1-(1-ethyl-4-hydroxy-1H-pyrazol-3-yl)ethanone as a yellow oil (2.16 g, 87%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. extractionextracted with CH2Cl2 (4×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e719044d4cf4707bcbd923381baa437
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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