Potassium Carbonate → 8-(2-oxo-2H-benzo[cd]indol-1-yl)-octanoic acid benzyloxyamide

HRID 9085

Reaction equation

[CH2:1]([O:8][NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:20]1[C:28]2[C:23]3[C:24](=[CH:29][CH:30]=[CH:31][C:22]=3[C:21]1=[O:32])[CH:25]=[CH:26][CH:27]=2.C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:8][NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:20]1[C:28]2[C:23]3[C:24](=[CH:29][CH:30]=[CH:31][C:22]=3[C:21]1=[O:32])[CH:25]=[CH:26][CH:27]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 67222benz(cd)indol-2(1H)-one

HCID 113364038-Bromo-octanoic acid benzyloxyamide

Product 1

HCID 865918818-(2-oxo-2H-benzo[cd]indol-1-yl)-octanoic acid benzyloxyamide

Procedure

In a manner analogous to that of example 1(b), 8-bromo-octanoic acid benzyloxyamide 0.49 g, 1.5 mmol) was reacted with benzo[cd]indol-2(1H)-one (0.25 g, 1.5 mmol) in the presence of potassium carbonate (0.2 g, 1.4 mmol) to give 8-(2-oxo-2H-benzo[cd]indol-1-yl)-octanoic acid benzyloxyamide as an amorphous solid (yield 0.12 g, 19%; purified by column chromatography using silica gel and ethyl acetate:heptane=1:1 as an eluent). MS (M+H+)=417.

Sources & evidence

ORD record: ord-dce42a25d6154aac814679c0cf4274dc
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091229B2

Linked notes

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