5-Chlorooxindole → 5-Chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one

HRID 2120213Notes

Reaction equation

HRID 2120213 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH:12]([C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([CH:32]([CH3:34])[CH3:33])[C:22]=1[O:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[CH:18]=O)([CH3:14])[CH3:13]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:18][C:17]1[CH:16]=[C:15]([CH:12]([CH3:14])[CH3:13])[C:22]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:21]([CH:32]([CH3:34])[CH3:33])[CH:20]=1

Participants

3

Reactant 2

HCID 1528015-ChlorooxindoleHCID 225711303,5-Diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

Product 1

HCID 537278155-Chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one

Procedure

5-Chloro-2-oxindole was condensed with 3,5-diisopropyl-4-(2-morpholin-4-yl-ethoxy)-benzaldehyde using method B to give 5-chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one as a brownish-orange solid which was reduced using method E to give 1.3 g (100%) of 5-chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzyl]-1,3-dihydroindol-2-one as a yellow/orange foam.

Sources & evidence

ORD record
ord-2eb1e8375156461e908d7eba10b4b648
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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