Triethylamine → HCID 57447005, compound

Participants

Reaction Steps

Triethylamine (50.0 mL, 358 mmol) and potassium carbonate (40 g, 290 mmol) were added to a solution of 4-chloro-3-nitroquinoline (49.6 g, 238 mmol) in tetrahydrofuran (THF) (100 mL) and chloroform (250 mL). Ethyl 4-aminobutyrate hydrochloride (43.8 g, 262 mmol) was added in portions over a period of five minutes during which time an ice bath was used to cool the reaction. The reaction was stirred with cooling for 30 minutes, allowed to warm to ambient temperature, and stirred overnight. An analysis by thin layer chromatography (TLC) indicated the presence of 4-chloro-3-nitroquinoline. Additional ethyl 4-aminobutyrate hydrochloride (8.0 g, 48 mmol) was added, and the reaction was stirred at ambient temperature for one hour and then heated at reflux for two hours. Additional triethylamine (20 mL) was added, and the reaction was heated at reflux for one hour, cooled to ambient temperature, washed with water (3×100 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 63.8 g of ethyl 4-(3-nitroquinolin-4-ylamino)butyrate as a yellow solid.

Provenance & Evidence