Hydrochloric Acid → HCID 178522923, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of 4-chlorobenzylamine (0.45 mL) in 5 mL of toluene is added 1.84 mL of a 2.0 M solution of trimethylaluminum in toluene. The solution is stirred for 5 min at 0° C. and then 0.20 g of ethyl 6,7,8-trifluoro-4-hydroxy-3-quinolinecarboxylate (Tetrahedron 48, 29 (1992)) is added. The solution is stirred at 0° C. for an additional 30 min and then it is stirred 18 h at 25° C. The mixture is poured onto a mixture of 50 mL of 3 M hydrochloric acid and 50 mL of crushed ice. The mixture is extracted with three successive 75 mL portions of ethyl acetate. The combined extracts are dried (MgSO4) and the solvent is evaporated at reduced pressure. The residue is dissolved in a small volume of ethyl acetate and hexanes is added until the solution becomes cloudy. The mixture is then allowed to stand for 1 h. Filtration of this mixture gives the desired amide as 0.25 g of a solid.

Provenance & Evidence