2-Chloroquinoline → 2-(4-(2-Quinolinyloxy)phenoxy)propanoic acid

Participants

Reaction Steps

The disodium salt of 2-(4-hydroxyphenoxy)propionic acid was made by dissolving the acid (9.1 gm, 0.05 mole) in 50 ml of DMSO and adding a solution of sodium hydroxide (4.4 gm, 0.11 mole) in 13 ml of water. The mixture was stirred for 30 min. and warmed to 55° C. at which time a solution of 2-chloroquinoline (8.2 gm, 0.050 mole) in 20 ml of DMSO was added. The reaction mixture was heated at 97°-108° for 1.5 hr. and then at 122°-125° for one hour longer. At the end of this time the mixture was poured into 600 ml of cold water and acidified. It was allowed to stand until solids formed which were taken up in toluene. From this 6.5 gm of 2-(4-(2-quinolinyloxy)phenoxy)propanoic acid were obtained.

Provenance & Evidence