4-Chlorobenzaldehyde → Z-6-chloro-3-(4-chloro-benzylidene)-1,3-dihydro-indol-2-one

HRID 556450Notes

Reaction equation

HRID 556450 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:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.N1CCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:17]/[C:16]3[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 962924Z-6-chloro-3-(4-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 4-chlorobenzaldehyde (12.9 g, 92 mmol) (Aldrich) in methanol (100 mL) was added pyrrolidine (6.55 g, 92 mol) (Aldrich) dropwisely. The mixture was then heated at 70° C. for 3 h. After cooling to 4° C., the resulting precipitate was collected and dried to give 21 g of E/Z-6-chloro-3-(4-chloro-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid. MS: 291 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-cd52e99667f94e9d846ada9a0ff9f54e
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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