Water → HCID 64793275, compound

To a solution of 5-amino-2-methylphenol (7.38 g, 59.9 mmol) in tetrahydrofuran (30 mL) was added water (30 mL) in which sodium hydrogen carbonate (6.00 g, 71.9 mmol) has been suspended, and the mixture was vigorously stirred at room temperature. 3-(Trifluoromethyl)benzoyl chloride (15.0 g, 71.9 mmol) was added dropwise to the mixture under ice-cooling, and the mixture was stirred at room temperature for 24 hr. The aqueous layer of the reaction mixture was separated, and the organic layer was diluted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and was filtrated, and the solvent was evaporated under reduced pressure. A mixture of the obtained residue, methanol (30 mL) and 2N aqueous sodium hydroxide solution (30 mL) was stirred at room temperature for 24 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and decolorized with activated carbon. The insoluble material was filtered off through a pad with two layers of silica gel and celite. The solvent was evaporated under reduced pressure, and the obtained solid was washed with a mixed solvent of ethyl acetate and hexane to give the title compound (14.8 g, 84%) as a white powder.

1. temperaturecooling
2. stirringthe mixture was stirred at room temperature for 24 hr
3. customThe aqueous layer of the reaction mixture was separated
4. additionthe organic layer was diluted with ethyl acetate
5. washwashed with saturated brine
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. filtrationwas filtrated
8. customthe solvent was evaporated under reduced pressure
9. additionA mixture of the obtained residue, methanol (30 mL) and 2N aqueous sodium hydroxide solution (30 mL)
10. stirringwas stirred at room temperature for 24 hr
11. additionWater was added to the reaction mixture
12. extractionthe mixture was extracted with ethyl acetate
13. washThe extract was washed with saturated brine
14. dry with materialdried over anhydrous magnesium sulfate
15. filtrationThe insoluble material was filtered off through a pad with two layers of silica gel and celite
16. customThe solvent was evaporated under reduced pressure
17. washthe obtained solid was washed with a mixed solvent of ethyl acetate and hexane

ORD record

ord-221c45a180cc4fdfa057f83f9b4db1a2

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2