Pyrrolidine → Z-6-chloro-3-[5-chloro-2-(4-methoxy-phenoxy)-benzylidene]-1,3-dihydro-indol-2-one

HRID 504523Notes

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]=[CH:15][C:16]([O:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[C:17]([CH:20]=1)[CH:18]=O.N1CCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:18]/[C:17]3[CH:20]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To the mixture of 6-chlorooxindole (8.3 g, 49.7 mmol) and 5-chloro-2-(4-methoxy-phenoxy)-benzaldehyde (13 g, 49.7 mmol) in methanol (100 mL) was added pyrrolidine (4.1 mL, 49.5 mmol) dropwise. The mixture was then heated at 70° C. for 3 h. After cooled to room temperature, the mixture was filtered and the precipitate was collected, dried to give the title compound as a yellow solid (15.5 g).

Workup

temperatureAfter cooled to room temperature
filtrationthe mixture was filtered
customthe precipitate was collected
customdried

Sources & evidence

ORD record: ord-01b01f74634547909e755b689325e402
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776875B2

Reaction notes

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