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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1913728Generated: October 25, 2026

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

https://huagongshe.com/reaction/1913728

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 numberUS08609705B2
Source datasetuspto-grants-2013_12
ORD IDord-9a73719daec24487a09b4c3ec582c503
Source noteuspto-grants-2013_12