Pyridine → N-[3-chloro-6-hydroxy-2-trifluoromethylphenyl]isonicotinamide
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([Cl:12])[CH:5]=[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:12][C:6]1[C:7]([C:8]([F:9])([F:10])[F:11])=[C:2]([NH:1][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[C:3]([OH:13])=[CH:4][CH:5]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 0.75 g of 2-amino-4-chloro-3-trifluoromethylphenol, 0.84 g of WSC, 0.42 g of isonicotinic acid and 5 ml of pyridine was stirred while heating at 80° C. for three hours. To the reaction mixture, 0.1 g of isonicotinic acid was added, and the reaction mixture was stirred while heating for further 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-[3-chloro-6-hydroxy-2-trifluoromethylphenyl]isonicotinamide.
Workup
- stirringthe reaction mixture was stirred
- temperaturewhile heating for further three hours
- 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
Sources & evidence
- ORD record
- ord-ea9d277993ee462bb78edb24b034ba26
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242133B2
Reaction notes
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