Pyrrole-2-carboxaldehyde → HCID 59973116, compound

HRID 428645Notes

Reaction equation

HRID 428645 reaction equation
[Br: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[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=O>CC(O)C>[Br: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:17]\[C:13]1[NH:12][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 6111935-Bromo-2-oxindole2×

Product 1

HCID 59973116HCID 59973116, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 5-bromo-1,3-dihydro-2H-indol-2-one (3.10 g, 14.62 mmol) (Starting Material 6) and pyrrole-2-carboxaldehyde (1.46 g, 15.35 mmol) (Aldrich) in 2-propanol (73 mL) was treated with 10-12 drops of piperidne. The reaction mixture was heated at reflux for 20 h and then allowed to cool to 23° C., at which time, the reaction mixture was filtered. The resulting solid was washed well with hexanes, followed by petroleum ether, and then allowed to air dry to provide pure (Z)-5-bromo-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a yellow solid which was used without further purification. (Yield 4.01 g, 95%; mp 267-268° C.).

Workup

  1. additionwas treated with 10-12 drops of piperidne
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 20 h
  4. filtrationthe reaction mixture was filtered
  5. washThe resulting solid was washed well with hexanes
  6. customto air dry

Sources & evidence

ORD record
ord-e029f52df97f4e8e8e75bbe6f63996df
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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