Oxindole → 3-[(3-Methyl-1H-pyrrol-2-yl)methylidene]-1,3-dihydro-2H-indol-2-one

HRID 1761145Notes

Reaction equation

HRID 1761145 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][C:12]1[CH:16]=[CH:15][NH:14][C:13]=1[CH:17]=O>N1CCCCC1.C(O)C>[CH3:11][C:12]1[CH:16]=[CH:15][NH:14][C:13]=1[CH:17]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

5

Reactant 2

HCID 321710OxindoleHCID 114235663-methyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 600442353-[(3-Methyl-1H-pyrrol-2-yl)methylidene]-1,3-dihydro-2H-indol-2-oneYield 67.4%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 133.0 mg of oxindole, 130.9 mg of the 3-methylpyrrole-2-carboxaldehyde, and 3 drops of piperidine in 2 mL of ethanol was stirred at 90° C. for 3 h. After cooling, the precipitate was filtered, washed with cold ethanol, and dried to yield 150.9 mg (67%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washwashed with cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-ca49b6780b1b4ed498cb9eab8dd229a3
Source dataset
uspto-grants-2005_01
Patent number
US06846839B1

Reaction notes

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