Sodium Hydroxide → HCID 9841482, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-[i-propyl-(1,1,3,3-tetramethyl-1,3-dihydro-isobenzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 86, 0.007 g) in 5 mL of ethanol was treated with 2 mL of 5M sodium hydroxide solution and the resulting solution was heated at 55° C. for 2 hours. The volatiles were removed by distillation in vacuo and the residue was acidified using hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate and evaporated to a residue which was subjected to preparative reverse phase HPLC, using 10% water in acetonitrile as the mobile phase, to afford the title compound (0.0064, 90%) as a white solid. 1H NMR (300 MHz, acetone-d6): δ 7.78 (d, 2H, J=8.9 Hz), 7.32 (d, 1H, J=7.8 Hz), 7.04 (dd, 1H, J=7.8 J=1.8 Hz), 7.00 (d, 1H, J=1.7 Hz), 6.56 (d, 2H, J=9.0 Hz), 4.46 (heptet, 1H, J=6.5 Hz), 1.50 (s, 6H), 1.47 (s, 6H), 1.15 (d, 6H, J=6.5 Hz).

Provenance & Evidence