p-Fluoronitrobenzene → 3-(1-cyano-1-methylethyl)-N-[4-methoxy-3-(4-nitrophenoxy)phenyl]benzamide

HRID 2190410Notes

Reaction equation

HRID 2190410 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([OH:20])[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].F[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

4

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 673126173-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methoxyphenyl)benzamide

Product 1

HCID 673133033-(1-cyano-1-methylethyl)-N-[4-methoxy-3-(4-nitrophenoxy)phenyl]benzamideYield 83.4%

Procedure

Using 3-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methoxyphenyl)benzamide (1.55 mg, 5.00 mmol), 1-fluoro-4-nitrobenzene (0.78 g, 5.50 mmol) and potassium carbonate (0.69 g, 5.00 mmol), and in the same manner as in Example A18(ii), the title compound (1.80 g, 83%) was obtained as a white powder.

Sources & evidence

ORD record
ord-10a673a7c8364db59cdf72f18a335591
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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