Benzenepropanoyl chloride → N-(3,3-dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-phenyl-propionamide

HRID 2235412Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[N:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6](=[O:19])[C:5]2([CH3:21])[CH3:20].[C:22]1([CH2:28][CH2:29][C:30](Cl)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:21][C:5]1([CH3:20])[C:4]2[C:8](=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([NH:1][C:30](=[O:31])[CH2:29][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:3]=2)[N:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1=[O:19]

Participants

Reactant 2

HCID 64801Benzenepropanoyl chloride

HCID 178027445-Amino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-one

Product 1

HCID 23092643N-(3,3-dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-phenyl-propionamideYield 99.7%

Procedure

N-(3,3-Dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-phenyl-propionamide (1.17 g) is synthesized from A8 (807 mg) and freshly prepared 3-phenyl-propionyl chloride (0.5 ml; 3,3 mmol) as described in Example 1a.

Sources & evidence

ORD record: ord-c59c236d61074a65b91e010b517653df
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714010B2

Reaction notes

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