Triethylamine → Ethyl 4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 3-neck, 5 L flask was charged with ethyl 8-chloro-4-oxo-5 -(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate (5A) (100 g, 0.3 mol), ethanol (1250 mL, 12.5 mL/g) and triethylamine (220 mL, 1.6 mol). The vessel was then charged with 10 g of 10% Pd/C (50% wet) at 5° C. The reaction was stirred vigorously under hydrogen atmosphere for 20 h at 5° C., after which time the reaction mixture was concentrated to a volume of approximately 150 mL. The product, ethyl 4-oxo-5-(trifluoromethyl)-1H-quinoline-3-carboxylate (6), was taken directly into the next step as a slurry with Pd/C.

Provenance & Evidence