2-Chlorophenol → 2-(2-Chlorophenoxy)-5-(3,4-dimethoxybenzoyl)pyridine

HRID 1031499Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

In dimethyl formamide (10 ml) was suspended 60% sodium hydride (dispersion in paraffin) (288 mg), to which was added dropwise a solution of 2-chlorophenol (926 mg) in dimethylformamide. When exothermic reaction and evolution of hydrogen gas ceased, 2-chloro-5-(3,4-dimethoxybenzoyl)pyridine (1 g) was added to the reaction mixture, followed by stirring for hours at 80° C. The reaction mixture was poured into ice-water, then precipitating substance was collected by filtration, and purified by means of a silica gel column chromatography [eluent: n-hexane+ethyl acetate (1:1)] to obtain 2-(2-chlorophenoxy)-5-(3,4-dimethoxybenzoyl)pyridine (1.1 g) as an oil.

Workup

customprecipitating substance
filtrationwas collected by filtration
custompurified by means of a silica gel column chromatography [eluent: n-hexane+ethyl acetate (1:1)]

Sources & evidence

ORD record: ord-79cd20f6fb6541acadbc883eb00f7b3f
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04954497

Reaction notes

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