Hydrochloric Acid → HCID 178522875, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of 4-chlorobenzylamine (0.52 mL) in 5 mL of toluene is added 2.13 mL of a 2.0 M solution of trimethylaluminum in tolune. The solution is stirred for 5 min at 0° C. and then a suspension of 0.50 g of ethyl 6-fluoro-4-hydroxy-3-quinolinecarboxylate (J. Amer. Chem. Soc., 69, 371 (1947)) in 5 mL of toluene is added. The solution is stirred at 0° C. for an additional 10 min and then it is stirred 18 h at 90° C. The mixture is cooled to 25° C. and it is poured onto a mixture of a large excess of 3 M hydrochloric acid and ice. After stirring the mixture vigorously for 30 min it is filtered. The solid is dissolved in 50 mL of warm glacial acetic acid and distilled water is added to the resulting solution until it is cloudy. The mixture is then allowed to stand for several hours at 5° C. Filtration of this mixture gives the desired amide as 390 mg of a solid.

Provenance & Evidence