Glyoxal → HCID 66920591, compound

HRID 1880340Notes

Reaction equation

HRID 1880340 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][N:8]=[CH:9][C:10](=[O:12])[CH3:11].[CH:13]([CH:15]=O)=[O:14]>O.CO.CCOC(C)=O>[OH:12][C:10]1[C:9]([C:13](=[O:14])[CH3:15])=[N:8][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:11]=1

Participants

6

Reactant 2

HCID 7860GlyoxalHCID 66920377HCID 66920377, compound

Product 1

HCID 66920591HCID 66920591, compoundYield 2.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-oxopropanal pyridin-2-ylhydrazone (6.12 g, 37.5 mmol) and glyoxal (16.3 g, 12.9 mL, 113 mmol) in water (50 mL) and methanol (10 mL) was heated at reflux overnight. The mixture was cooled to room temperature, diluted with EtOAc and sequentially washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated. The crude material was passed over a plug of silica gel, eluting with heptane/EtOAc (1:2, 300 mL) to afford 1-(4-hydroxy-1-pyridin-2-yl-1H-pyrazol-3-yl)ethanone (199 mg, 2.6%).

Workup

  1. temperatureat reflux overnight
  2. washsequentially washed with saturated aqueous NaHCO3, saturated aqueous NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluting with heptane/EtOAc (1:2, 300 mL)

Sources & evidence

ORD record
ord-fd62b18bb256418f90b6e5ff762df091
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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