Piperidine → 3-[N-(3,5-dichlorophenyl)pyrrol-2-yl]-5-acetylaminoindolin-2-one

HRID 585094Notes

Reaction equation

HRID 585094 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[CH:14]=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:16]([NH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])C2)(=[O:18])[CH3:17].N1CCCCC1>C(O)C>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[CH:14]2[C:27]3[C:26](=[CH:22][CH:21]=[C:20]([NH:19][C:16](=[O:18])[CH3:17])[CH:28]=3)[NH:25][C:24]2=[O:29])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 27770161-(3,5-dichlorophenyl)-1H-pyrrole-2-carbaldehydeHCID 11206280N-(2-oxoindolin-5-yl)acetamide

Product 1

HCID 98656973-[N-(3,5-dichlorophenyl)pyrrol-2-yl]-5-acetylaminoindolin-2-oneYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.68 g (11 mmol) of 3-[N-(3,5-dichlorophenyl)pyrrole-2-carboxaldehyde are added to a solution of 2.12 g (11 mmol) of 5-acetylaminoindolin-2-one in 220 ml of ethanol containing 0.5 ml of piperidine. The reaction medium is heated under reflux for 3 hours. After cooling, the precipitate formed is drained, washed with twice 5 ml of ice-cold ethanol and dried under reduced pressure. 1.81 g (40%) of 3-[N-(3,5-dichlorophenyl)pyrrol-2-yl]-5-acetylaminoindolin-2-one are thus obtained in the form of a yellow solid whose characteristic is the following: melting point=267° C.

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. washwashed with twice 5 ml of ice-cold ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-f118c9603e6248938a577aa879b4df7d
Source dataset
uspto-grants-2005_08
Patent number
US06930124B2

Reaction notes

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