1H-Pyrazole-3-carbaldehyde → HCID 178487281, compound

HRID 858483Notes

Reaction equation

HRID 858483 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1.[NH:20]1[CH:24]=[CH:23][C:22]([CH:25]=O)=[N:21]1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)C.C1C=CC=CC=1>[CH3:19][O:18][C:16]1[CH:15]=[CH:14][C:3]2[N:4]([C:5]3[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=3)[C:25]([C:22]3[CH:23]=[CH:24][NH:20][N:21]=3)=[N:1][C:2]=2[CH:17]=1

Participants

6

Reactant 3

HCID 122183831H-Pyrazole-3-carbaldehydeHCID 21876179HCID 21876179, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 178487281HCID 178487281, compoundYield 16.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A mixture of 2-(4-{[2-amino-4-(methyloxy)phenyl]amino}phenyl)ethanol (step 2 of Example 71, 1.95 g, 7.56 mmol), pyrazol-3-carbaldehyde (726 mg, 7.56 mmol) in ethanol (45 ml) was heated at reflux temperature for 2 h. After cooling, the mixture was concentrated. A mixture of the residue, lead tetraacetate (4.61 g, 8.32 mmol) in benzene (50 ml) was stirred at room temperature for 16 h. The mixture was quenched with saturated NaHCO3 aqueous solution (150 ml). The whole was extracted with ethyl acetate (150 ml×4). The organic layer was washed with water (100 ml×5), brine (50 ml), dried (MgSO4), and concentrated. Purification by flash column chromatography eluting with dichloromethane/methanol (gradient elution from 20:1 to 10:1) to afford 408 mg (16%) of the title compound as an amber solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated
  5. customThe mixture was quenched with saturated NaHCO3 aqueous solution (150 ml)
  6. extractionThe whole was extracted with ethyl acetate (150 ml×4)
  7. washThe organic layer was washed with water (100 ml×5), brine (50 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customPurification by flash column chromatography
  11. washeluting with dichloromethane/methanol (gradient elution from 20:1 to 10:1)

Sources & evidence

ORD record
ord-00faabaa4e5c493d916bfe4e7d3af3fd
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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