Sulfuric Acid → 5-(1-phenyl-1H-pyrazol-5-yl)indolin-2-one

HRID 588272Notes

Reaction equation

HRID 588272 reaction equation
C(O[CH:4](OCC)[C:5]#[C:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10]2)C.[C:20]1([NH:26][NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(#N)C.O>[C:20]1([N:26]2[C:6]([C:7]3[CH:8]=[C:9]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:11](=[O:16])[CH2:10]4)=[CH:5][CH:4]=[N:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 1118Sulfuric Acid2×HCID 7516PhenylhydrazineHCID 516892Sodium BicarbonateHCID 90417345HCID 90417345, compound

Product 1

HCID 904178015-(1-phenyl-1H-pyrazol-5-yl)indolin-2-oneYield 42.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(3,3-diethoxyprop-1-ynyl)indolin-2-one (100 mg, 0.39 mmol) in acetonitrile (5 ml) were added phenyl hydrazine (38 μL, 0.38 mmol) and sulfuric acid (52 μL, 0.98 mmol), and the mixture was stirred for 3 h at room temperature, then the mixture was stirred for 2 h at 50° C. The reaction mixture was poured into water (50 mL), and the resulting precipitate was filtered and dried. The precipitated was dissolved in acetonitrile (5 mL), then water (52 μL, 3.9 mmol) and sulfuric acid (93 μL, 1.75 mmol) were added. The mixture was heated at 80 C for 4 h. The mixture was cooled to room temperature, and then neutralized with sat. NaHCO3. The mixture was extracted with CHCl3/EtOAc 3 times. The combined organic extracts were washed with sat. NaCl, dried over Na2SO4, and evaporated in vacuo. The residue purified by column chromatography (EtOAc/n-hexane) to give the title compound as a brown solid (44 mg, 41%).

Workup

  1. stirringthe mixture was stirred for 2 h at 50° C
  2. filtrationthe resulting precipitate was filtered
  3. customdried
  4. dissolutionThe precipitated was dissolved in acetonitrile (5 mL)
  5. temperatureThe mixture was heated at 80 C for 4 h
  6. temperatureThe mixture was cooled to room temperature
  7. extractionThe mixture was extracted with CHCl3/EtOAc 3 times
  8. washThe combined organic extracts were washed with sat. NaCl
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuo
  11. customThe residue purified by column chromatography (EtOAc/n-hexane)

Sources & evidence

ORD record
ord-789a5e75e1a8482cb753c94eb7d01643
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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