Hydrochloric Acid → HCID 178487281, compound

HRID 724125Notes

Reaction equation

HRID 724125 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=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].Cl>C(O)C.C1C=CC=CC=1.CO>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=3)[C:25]([C:22]3[CH:23]=[CH:24][NH:20][N:21]=3)=[N:1][C:2]=2[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 122183831H-Pyrazole-3-carbaldehydeHCID 21876179HCID 21876179, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 178487281HCID 178487281, compoundYield 16.1%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 887MethanolSolvent2×

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 1.37 mmol) in methanol (4 ml) was added 10% HCl in methanol (2 ml) at room 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. extractionextracted with ethyl acetate (150 ml×4)
  6. washThe organic layer was washed with water (100 ml×5), brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customPurification by flash column chromatography
  10. washeluting with dichloromethane/methanol (gradient elution from 20:1 to 10:1)

Sources & evidence

ORD record
ord-9a7fdb2d16994c10b8bd382942d85b1d
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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