Oxindole → 3-[(4-Methylthiophen-2-yl)methylidene]-1,3-dihydro-2H-indol-2-one

HRID 1761144Notes

Reaction equation

HRID 1761144 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:13]=[C:14]([CH:17]=O)[S:15][CH:16]=1>N1CCCCC1.C(O)C>[CH3:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])[S:15][CH:16]=1

Participants

5

Reactant 2

HCID 321710OxindoleHCID 27955264-methylthiophene-2-carbaldehyde

Product 1

HCID 696317043-[(4-Methylthiophen-2-yl)methylidene]-1,3-dihydro-2H-indol-2-oneYield 61.1%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 133.0 mg of oxindole, 151.2 mg of the 4-methylthiophene-2-carboxaldehyde, and 3 drops of piperidine in 3 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 147.3 mg (61%) 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-974b62aaf1e345dca220ffda5645d043
Source dataset
uspto-grants-2005_01
Patent number
US06846839B1

Reaction notes

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