Potassium Hydroxide → 3-(3,5-dichlorophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one

Temperature

75 °C

To 2-chloro-3-(3,5-dichlorophenoxy)-4-(trifluoromethyl)pyridine (2.10 g, 6.10 mmol) in tert-butanol (25 mL) was added potassium hydroxide (1.03 g, 18.4 mmol). The reaction mixture was placed in an oil bath and heated at 75° C. After 48 hours, the reaction mixture was allowed to cool to room temperature and was quenched with saturated aqueous ammonium chloride (25 mL) and diluted with water (25 mL). The mixture was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (2×50 mL) and the solvent was evaporated under reduced pressure to yield a solid. This was adsorbed onto silica and purified by column chromatography on a pre-packed silica gel Redi Sep 40 gram column, eluting with 0-5% methanol in CH2Cl2 to afford the title compound. 1H NMR (DMSO-d6) δ 12.69 (s, 1H), 7.58 (d, J=6.8 Hz, 1H), 7.32-7.30 (m, 1H), 7.10-7.08 (m, 2H), 6.48 (d, J=6.8 Hz, 1H). HRMS (M+1)=323.9800.

1. customThe reaction mixture was placed in an oil bath
2. temperatureto cool to room temperature
3. customwas quenched with saturated aqueous ammonium chloride (25 mL)
4. additiondiluted with water (25 mL)
5. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
6. washThe combined organic extracts were washed with water (2×50 mL)
7. customthe solvent was evaporated under reduced pressure
8. customto yield a solid
9. custompurified by column chromatography on a pre-packed silica gel Redi Sep 40 gram column
10. washeluting with 0-5% methanol in CH2Cl2

ORD record

ord-26d671dc25234f96887b148b63054e9d

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404856B2