4-Chlorobenzaldehyde → 3-(4-Chlorobenzylidene)indolin-2-one

HRID 1805303Notes

Reaction equation

HRID 1805303 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].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.N1CCCC1>>[Cl:11][C:12]1[CH:19]=[CH:18][C:15](/[CH:16]=[C:3]2\[C:2](=[O:10])[NH:1][C:9]3[C:4]\2=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 31268PyrrolidineHCID 321710Oxindole

Product 1

HCID 53982193-(4-Chlorobenzylidene)indolin-2-oneYield 93.9%

Procedure

Oxindole (0.13 g, 1 mmol), 4-chlorobenzaldehyde (0.17 g, 1.2 mmol) were mixed in alcohol; then pyrrolidine (0.17 ml, 2 mmol) was added. The mixture was refluxed for 3 hours. The formed precipitates was collected by filtration and washed with alcohol twice to give the title compound as yellow powder (0.24 g, 92%). LC/MS m/e calcd. for C15H10ClNO 255, observed (M+H)+: 256.1.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customThe formed precipitates
  3. filtrationwas collected by filtration
  4. washwashed with alcohol twice

Sources & evidence

ORD record
ord-4d1c8ca6092e49eeb8520ba43c67ef62
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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