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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 884965Generated: October 26, 2026

Pyridine → 3-chloro-N-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamide

https://huagongshe.com/reaction/884965

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant3-Chloropyridine-4-carboxylic acidHCID 2735816—
Reactant2-Amino-5-chloro-4-(trifluoromethyl)phenolHCID 14011736—
SolventWaterHCID 962—
Product3-chloro-N-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamideHCID 6688050757.3%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 0.50 g of 2-amino-5-chloro-4-trifluoromethylphenol, 0.36 g of 3-chloroisonicotinic acid, 0.56 g of WSC and 5 ml of pyridine was stirred while heating at 80° C. for three hours. The reaction mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate three times. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.46 g of 3-chloro-N-[4-chloro-2-hydroxy-5-trifluoromethylphenyl]isonicotinamide.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08242133B2
Source datasetuspto-grants-2012_08
ORD IDord-b57343f02c484e4e8a11ec8db9f5358d
Source noteuspto-grants-2012_08