Diisopropylamine → 2-Chloro-8-(trifluoromethyl)quinoline-3-carbaldehyde

Temperature

0 °C

To a cold solution of butyllithium (0.498 g, 1.7 mmol) in 2 mL dry THF at −20C. was added diisopropyl amine (0.192 g, 1.9 mmol) drop wise and reaction mixture was allowed to stir at 0° C. for 1 h. then reaction mixture was again cooled to −78° C. and a solution of 2-chloro-8-trifluoromethyl-quinoline (0.4 g, 1.70 mmol) in 4 mL dry THF was added drop wise continued stirring for 5-10 min then added ethyl formate (0.12 g, 1.7 mmol) drop wise, continued stirring for 0.5 h. n-Butyllithium was quenched with ammonium chloride solution and extracted with ether (3×10 mL). The combined organic layers were washed with brine solution, dried over sodium sulfate, concentrated under vacuum to get the crude compound. The crude residue was purified over silica gel (100-200 mesh) using 10% ethyl acetate: petroleum ether to afford the desired compound (0.15 g, 34%).

1. customreaction mixture
2. customreaction mixture
3. temperaturewas again cooled to −78° C.
4. stirringwise continued stirring for 5-10 min
5. customwas quenched with ammonium chloride solution
6. extractionextracted with ether (3×10 mL)
7. washThe combined organic layers were washed with brine solution
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated under vacuum
10. customto get the crude compound
11. customThe crude residue was purified over silica gel (100-200 mesh)

ORD record

ord-10295616d78d4866ab02a75862d5e291

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604055B2