Sodium Hydroxide → 4'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylic acid

Participants

Reaction Steps

1.25M sodium hydroxide solution (2.4 ml) was added to a solution of methyl 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2- carboxylate (A) (380 mg) in ethanol (5 ml). The solution was heated under reflux for 2 hours and then volatile material was removed by evaporation. The residue was dissolved in water (30 ml) and the solution acidified to pH 4 with 2M hydrochloric acid. The precipitated solid was a collected, dried under high vacuum and recrystallised from ethanol to give 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylic acid (254 mg), as white crystals, m.p. 204°-205° C.; NMR (d6 -dimethylsulphoxide (d6 -DMSO)): 1.34(t,3H), 2.9(q,2H), 5.42(s,2H), 7.1(s,1H), 7.38-7.78(complex m,10H), 7.88(d,1H), 8.15(dd,1H), 12.74(br,1H); mass spectrum (negative fast atom bombardment [-ve FAB], DMSO/glycerol (GLY): 382 (M-H)-, 172; microanalysis found: C,78.0; H,5.4; N,4.05; C25H21NO3 requires: C,78.3; H,5.5; N,3.7%.

Provenance & Evidence