5-Chloro-salicylaldehyde → cyclopentanecarboxylic acid [3-(5-chloro-2-hydroxy-benzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-amide

HRID 2120204Notes

Reaction equation

HRID 2120204 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([NH:11][C:12]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:13])=[CH:7][CH:8]=2)[NH:3]1.[Cl:19][C:20]1[CH:27]=[C:24]([CH:25]=O)[C:23]([OH:28])=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([OH:28])=[C:24]([CH:27]=1)[CH:25]=[C:10]1[C:9]2[C:4](=[CH:5][C:6]([NH:11][C:12]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)=[O:13])=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:1]

Participants

3

Reactant 2

HCID 124815-Chloro-salicylaldehydeHCID 54539339Cyclopentanecarboxylic acid (2-oxo-2,3-dihydro-1H-indol-6-yl)-amide

Product 1

HCID 54448262cyclopentanecarboxylic acid [3-(5-chloro-2-hydroxy-benzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-amide

Procedure

Cyclopentanecarboxylic acid (2-oxo-2,3-dihydro-1H-indol-6-yl)-amide was condensed with 5-chlorosalicylaldehyde using method B to give cyclopentanecarboxylic acid [3-(5-chloro-2-hydroxy-benzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-amide which was reducted using method D to give 34.4 mg (68%) cyclopentanecarboxylic acid [3-(5-chloro-2-hydroxybenzyl)-2-oxo-2,3-dihydro-1H-indol-6-yl]-amide as an off-white crystalline solid.

Sources & evidence

ORD record
ord-6c1230440c534d4c9d1ddfd09eb51140
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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