5-Chlorooxindole → 5-(5-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2101550Notes

Reaction equation

HRID 2101550 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.[CH2:12]([O:14][C:15]([C:17]1[NH:18][C:19]([CH:23]=O)=[C:20]([CH3:22])[CH:21]=1)=[O:16])[CH3:13]>>[CH2:12]([O:14][C:15]([C:17]1[NH:18][C:19]([CH:23]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][C:6]2=[O:11])=[C:20]([CH3:22])[CH:21]=1)=[O:16])[CH3:13]

Participants

3

Reactant 2

HCID 1528015-ChlorooxindoleHCID 9855648Ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 672810735-(5-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 94%

Procedure

5-Chloro-1,3-dihydroindol-2-one (2.22 g, 13.2 mmol) was condensed with 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.43 g) using method E to give 4.1 g (94%) of the title compound as an orange solid.

Sources & evidence

ORD record
ord-7bed33c8cc09487ca046fdcd3ab08d32
Source dataset
uspto-grants-2009_08
Patent number
US07572924B2

Reaction notes

Loading…