Piperidine → 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one

HRID 352296Notes

Reaction equation

HRID 352296 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:16][C:17]1[NH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 1528015-Chlorooxindole

Product 1

HCID 404857155-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-oneYield 442.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-chlorooxindole (6.98 g, 41.6 mmol), 3,5-dimethyl-1H-pyrrole-2-carhoxaldehyde (5.12 g, 41.6 mmol) and piperidine (410 μL, 4.16 mmol) in 200 mL of EtOH was heated at reflux for 8 h. The reaction mixture was cooled to room temperature and filtered to give the title compound (4.50 g, 40%) as a red/orange solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f3af6ffb8fdf4661940e21a0a156ae5c
Source dataset
uspto-grants-2004_06
Patent number
US06747025B1

Reaction notes

Loading…