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

HRID 1913721

Reaktionsgleichung

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[OH:13].CCN=C=NCCCN(C)C.[C:25](O)(=[O:32])[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.N1C=CC=CC=1>O>[Cl:8][C:6]1[C:5]([C:9]([F:12])([F:10])[F:11])=[CH:4][C:3]([OH:13])=[C:2]([NH:1][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 0.70 g of 2-amino-4-chloro-5-trifluoromethylphenol, 0.79 g of WSC, 0.39 g of isonicotinic acid and 6 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 0.54 g of N-[5-chloro-2-hydroxy-4-trifluoromethylphenyl]isonicotinamide.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate three times
washThe combined organic layers were washed with water
dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-348e3e12355b483ea810ebef653cd69f
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08609705B2

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