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

HRID 1976182Notes

Reaction equation

HRID 1976182 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][S:14][C:13]=1[CH:17]=O>N1CCCCC1.C(O)C>[CH3:11][C:12]1[CH:16]=[CH:15][S: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 799113-Methyl-2-thiophenecarboxaldehydeHCID 321710Oxindole

Product 1

HCID 32759743-[(3-Methylthien-2-yl)methylene]-2-indolinoneYield 65%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 134.0 mg of oxindole, 151.4 mg of the 3-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 157.8 mg (65%) 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-a2100d78c5154d8eabc71b09e3e7dcae
Source dataset
uspto-grants-2001_05
Patent number
US06225335B1

Reaction notes

Loading…