Hydrochloric Acid → HCID 28401656, compound

Concentrated hydrochloric acid (5.8 ml) was added to an ethanol solution (100 ml) of N-(5-bromo-2-cyclopentyloxyphenyl)acetamide (3.4 g, 11.4 mmol), and the resulting mixture was stirred for 3 hours while heating under reflux. After the reaction mixture was cooled to room temperature, a 5N sodium hydroxide solution (14.2 ml) was added to obtain a pH of 11. The resulting mixture was then extracted with dichloromethane. The organic layer was washed with a saturated sodium chloride aqueous solution, and then concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1). The purified product was concentrated under reduced pressure to thereby obtain 2.97 g of oily pale yellow 5-bromo-2-cyclopentyloxyaniline (yield: 100%).

1. temperaturewhile heating
2. temperatureunder reflux
3. customto obtain a pH of 11
4. extractionThe resulting mixture was then extracted with dichloromethane
5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
6. concentrationconcentrated under reduced pressure
7. customThe residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)
8. concentrationThe purified product was concentrated under reduced pressure

ORD record

ord-113948156d4c41c281f290411a4d994c

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642619B2