4-Chlorobenzylamine → HCID 178487897, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 320 mg of ethyl 4-hydroxy-6-methoxy-3-quinolinecarboxylate (J. Amer. Chem. Soc., 68, 1204 (1946)) and 1.0 mL of 4-chlorobenzylamine is stirred for 1 h at 210° C. The mixture is cooled to 25° C. and it is diluted with 2.0 mL of toluene. The mixture is filtered and the filtrant is dissolved in a minimum volume of refluxing glacial acetic acid. The hot solution is treated with distilled water dropwise until it becomes cloudy, and it is allowed to cool to 25° C. The precipitate is collected by filtration and it is washed with a small amount of dilute aqueous acetic acid. It is dried in a stream of air and then it is dissolved in 7 mL of refluxing acetonitrile. The solution is allowed to cool to 25° C. and after an additional 2 h the precipitate is collected by filtration. The solid is dried for 48 h at torr and 85° C. This procedure gives the title compound as 64 mg of a light tan solid.

Provenance & Evidence