Trichloroacetyl chloride → 2,2,2-trichloro-N-5-quinolinylacetamide

To a solution of 5-aminoquinoline (1.0 g, 6.9 mmol) and triethylamine (1.0 mL, 7.2 mmol) in dichloromethane (40 mL) was added trichloroacetyl chloride (1.4 g, 7.7 mmol) at 0° C., and the mixture was stirred at room temperature for 90 minutes. The reaction solution was concentrated, and to the residue was added ethyl acetate, and the resulting mixture was extracted three times with 1 N hydrochloric acid. The aqueous layers were combined and neutralized with an aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was washed with diisopropyl ether and collected by filtration to obtain the title compound (1.9 g, yield 94%) as colorless crystals.

1. concentrationThe reaction solution was concentrated
2. additionto the residue was added ethyl acetate
3. extractionthe resulting mixture was extracted three times with 1 N hydrochloric acid
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with water and saturated brine
6. dry with materialdried over magnesium sulfate
7. filtrationThe solid was filtered off
8. concentrationthe filtrate was concentrated
9. washThe residue was washed with diisopropyl ether
10. filtrationcollected by filtration

ORD record

ord-6ca5df09d98040e581c09283e51a93f1

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795267B2