5-Methyl-2-thiophenecarboxaldehyde → 3-[(2-Methylthien-5-yl)methylene]-2-indolinone

HRID 1976181Notes

Reaction equation

HRID 1976181 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[S:16][C:15]([CH:17]=O)=[CH:14][CH:13]=1>N1CCCCC1.C(O)C>[CH3:17][C:15]1[S:16][C:12]([CH:11]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 321710Oxindole

Product 1

HCID 43748903-[(2-Methylthien-5-yl)methylene]-2-indolinoneYield 99%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 134.0 mg of oxindole, 151.42 mg of the 5-methylthiophene-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 237.8 mg (99%) 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-a2e12dcac9f1401aadeed37f59e9470e
Source dataset
uspto-grants-2001_05
Patent number
US06225335B1

Reaction notes

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