Hydrochloric Acid → 1-(5-Chloro-8-hydroxy-7-quinolinyl)ethanone

Temperature

0 °C

A mixture of 5-chloro-8-quinolinol (6.67 g, 37.1 mmol, from Aldrich), aluminum trichloride (20.00 g, 150.0 mmol), and acetyl chloride (12.1 mL, 170 mmol) was stirred at 0° C. for 4 hours, then heated at 130° C. for 12 hours, cooled, and decomposed with water (39 mL) (caution!) and conc. HCl (13 mL). The solid product was filtered, and dried under reduced pressure. The solid obtained was then dissolved in 50 mL of water. To the solution was added 100 mL of dichloromethane. The mixture was cooled with an ice bath and its pH was adjusted to 4 with 20% NaOH. The mixture was filtered under reduced pressure. The solid collected was washed with water and air dried to give the desired product (˜2 g). The layers of the filtrate were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine, dried over magnesium sulfate and concentrated to give additional desired product (total 5.6 g, 68%). LCMS calculated for C11H9ClNO2 (M+H)+: m/z=222.0; Found: 222.0.

1. temperatureheated at 130° C. for 12 hours
2. temperaturecooled
3. filtrationThe solid product was filtered
4. customdried under reduced pressure
5. customThe solid obtained
6. temperatureThe mixture was cooled with an ice bath
7. filtrationThe mixture was filtered under reduced pressure
8. customThe solid collected
9. washwas washed with water and air
10. customdried

ORD record

ord-97c455dde0b94faf9031d00d9189945b

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680108B2