3-Chlorobenzaldehyde → Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one

HRID 2102701Notes

Reaction equation

HRID 2102701 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.N1CCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:16]/[C:15]3[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 57507271Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 6-chlorooxindole (16.2 g, 92 mmol) (Crescent) and 3-chlorobenzaldehyde (12.9 g, 92 mmol) (Aldrich) in methanol (109 mL) was added pyrrolidine (6.55 g, 92 mmol) (Aldrich) dropwisely. The mixture was then heated at 70° C. for 3 hours. After cooling to 4° C., the resulting precipitate was collected and dried to give E/Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid. (Yield 25.2 g, 95%).

Workup

  1. temperatureAfter cooling to 4° C.
  2. customthe resulting precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-589805c72a224855b9d32e1556fdcd4e
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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