5-Chlorooxindole → 5-chloro-3-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one

HRID 2120221Notes

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.[CH3:12][N:13]([CH3:26])[CH2:14][CH2:15][CH2:16][C:17]1[C:18]([CH3:25])=[C:19]([CH:23]=O)[NH:20][C:21]=1[CH3:22]>>[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:23][C:19]1[NH:20][C:21]([CH3:22])=[C:17]([CH2:16][CH2:15][CH2:14][N:13]([CH3:12])[CH3:26])[C:18]=1[CH3:25]

Participants

Reactant 2

HCID 1528015-Chlorooxindole

HCID 219257584-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 544268965-chloro-3-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-oneYield 53%

Procedure

5-Chloro-1,3-dihydroindol-2-one (167 mg, 1.0 mmol) was condensed with 4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (208 mg, 1.0 mmol) using method B to give 188.7 mg (53%) of 5-chloro-3-[4-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one as a brown solid.

Sources & evidence

ORD record: ord-e5b72272b85c41e0b7eb6259bf946463
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689806B1

Reaction notes

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