Acetic Acid → 1-[4-hydroxy-1-(3-methoxyphenyl)-1H-pyrazol-3-yl]ethanone

HRID 1880333Notes

Reaction equation

HRID 1880333 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][N:10]=[CH:11][C:12](=[O:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.[C:15](O)(=[O:17])[CH3:16].C(C=O)=O>CCOC(C)=O>[OH:14][C:12]1[C:11]([C:15](=[O:17])[CH3:16])=[N:10][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7860GlyoxalHCID 669204522-Oxopropanal (3-methoxyphenyl)hydrazone

Product 1

HCID 669205401-[4-hydroxy-1-(3-methoxyphenyl)-1H-pyrazol-3-yl]ethanoneYield 10%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-oxopropanal (3-methoxyphenyl)hydrazone (2.88 g, 14.5 mmol), acetic acid (20 mL) and glyoxal (6.3 g, 5.0 mL, 43 mmol) were heated at reflux overnight. The reaction was cooled to room temperature, diluted with EtOAc and washed with saturated aqueous NaCl. The black sludge was removed by decantation and the filtrate was washed with more saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Purify by CombiFlash (80 g column, 0-50% heptane/EtOAc gradient) to afford 1-[4-hydroxy-1-(3-methoxyphenyl)-1H-pyrazol-3-yl]ethanone (330 mg, 10%).

Workup

  1. temperaturewere heated
  2. temperatureat reflux overnight
  3. washwashed with saturated aqueous NaCl
  4. customThe black sludge was removed by decantation
  5. washthe filtrate was washed with more saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurify by CombiFlash (80 g column, 0-50% heptane/EtOAc gradient)

Sources & evidence

ORD record
ord-7ef0486bef9141a1b6a334d3a1fe5a62
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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