p-Fluoronitrobenzene → 3-(1-cyanocyclopropyl)-N-[4-methyl-3-(4-nitrophenoxy)phenyl]benzamide

HRID 2190443Notes

Reaction equation

[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([OH:19])[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].F[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2]

Participants

Reactant 3

HCID 9590p-Fluoronitrobenzene

HCID 11430Potassium Carbonate

HCID 673125573-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamide

Product 1

HCID 673126343-(1-cyanocyclopropyl)-N-[4-methyl-3-(4-nitrophenoxy)phenyl]benzamide

Procedure

Using 3-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamide (1.46 g, 5.0 mmol), 1-fluoro-4-nitrobenzene (0.77 g, 5.5 mmol) and potassium carbonate (0.69 g, 5.0 mmol), and in the same manner as in Example A25(iii), the title compound (2.07 g, quantitatively) was obtained as a yellow oil.

Sources & evidence

ORD record: ord-7d5af6e1caed4f15bcd03f42a5fd805a
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324395B2

Reaction notes

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