Potassium Carbonate → HCID 20065036, compound

HRID 359475Notes

Reaction equation

HRID 359475 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15]([OH:19])=[C:14]([O:20][CH3:21])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15]([O:19][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[C:14]([O:20][CH3:21])[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 171604,5-DichloroguaiacolHCID 762582-Chloronicotinic acid

Product 1

HCID 20065036HCID 20065036, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloronicotinic acid and 4,5-dichloro-2-methoxyphenol are reacted in the presence of potassium carbonate in dimethylformamide to give 2-(4,5-dichloro-2-methoxyphenoxy)nicotinic acid, which is reacted with thionyl chloride in dichloroethane to be converted into the acid chloride. This acid chloride is reacted with ethoxymagnesium.diethyl malonate in a mixed solvent of chlorobenzene and ethanol, followed by treatment with conc. hydrochloric acid and acetic acid to obtain the acetyl compound. This acetyl compound is reacted with benzaldehyde in the presence of a small amount of sodium hydroxide in ethanol to give 2-(4,5-dichloro-2-methoxyphenoxy)-3-cinnamoylpyridine. This compound is treated with aluminium chloride to give 2-(4,5-dichloro-2-hydroxyphenoxy)-3-cinnamoylpyridine.

Sources & evidence

ORD record
ord-6a924dbb6f124ef9a8f7674db20db494
Source dataset
uspto-grants-1991_03
Patent number
US05001137

Reaction notes

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