Sodium Hydroxide → HCID 20094243, compound

Participants

Reaction Steps

1M Sodium hydroxide solution (5.0 ml) was added to a solution of methyl 2-[5-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy)methyl)benzoxazol-2-yl]benzoate (A) (443 mg) in methanol (20 ml) and the solution was left to stand for 72 hours. Volatile material was removed by evaporation and the residue was dissolved in methanol (10 ml). Water (40 ml) was added and the solution was neutralised with 1M acetic acid (5 ml). The precipitated solid was collected by filtration, dried by azeotroping with ethanol and triturated with ether to give 2-[5-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy)methyl)benzoxazol-2-yl]benzoic acid (152 mg), as a white powder, m.p. 229°-231° C; NMR (d6 -DMSO): 1.2(t, 3H), 1.7-1.85(m, 4H), 2.55-2.8(m, 6H), 5.3(s, 2H), 6.8(s, 1H), 7.55(dd, 1H), 7.65-7.9(m, 6H); mass spectrum (+ve FAB, DMSO/methanol/m-nitrobenzyl alcohol (NBA)): 429 (M+H)+ ; microanalysis, found: C, 70.7; H, 5.6; N, 6.1%; C26H24N2O4.0.5H2O requires: C, 71.2; H, 5.7; N, 6.4%.

Provenance & Evidence