Acetic Acid → HCID 86755987, compound

Participants

Reaction Steps

To a stirred suspension of cis-4-amino-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (4.49 g, 16.0 mmol) in 1,2-dichloroethane (100 mL) was added 3,5-bis(trifluoromethyl)benzaldehyde (2.6 mL, 16.0 mmol), followed by acetic acid (0.9 mL, 16.0 mmol). After 45 min, sodium triacetoxyborohydride (5.1 g, 24.0 mmol) was added, and the reaction was stirred at room temperature overnight. Water (75 mL) and ethyl acetate (75 mL) were added to the mixture which was then made basic to pH 10 with solid potassium carbonate. The mixture was then extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 8.17 g of crude product. Purification by silica gel chromatography using 0-30% ethyl acetate/hexanes as eluent afforded 4.90 g of the title compound (60%).

Provenance & Evidence