Hydrochloric Acid → 1-(8-Hydroxy-5-methylquinolin-7-yl)ethanone

温度

0 °C

A mixture of 5-methylquinolin-8-ol (5.91 g, 37.1 mmol, from ChemBridge), 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! with external ice-cooling if necessary) and conc. HCl (13 mL). The precipitate 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 the pH adjusted to 4 with slow addition of 20% NaOH. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine and dried over sodium sulfate. The suspension was filtered through a plug of cotton and concentrated to dryness. The residue was used directly in the next step (5.8 g, 78%). LCMS calculated for C12H12NO2 (M+H)+: m/z=202.1; Found: 202.0.

1. temperatureheated at 130° C. for 12 hours
2. temperaturecooled
3. filtrationThe precipitate was filtered
4. customdried under reduced pressure
5. customThe solid obtained
6. temperatureThe mixture was cooled with an ice bath
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with dichloromethane
9. washThe combined organic layers were washed with water, brine
10. dry with materialdried over sodium sulfate
11. filtrationThe suspension was filtered through a plug of cotton
12. concentrationconcentrated to dryness

ORDレコード

ord-fda3c65bbef748bcb621dd751cbffa39

出典データセット

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08680108B2