Ethanol → HCID 9927310, compound

Participants

Reaction Steps

A solution of 4-[methyl-(7-ethyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 21, 0.095 g, 0.27 mmol) in 10 mL of ethanol was treated with 2 mL (10 mmol) of 5M sodium hydroxide solution and the reaction mixture was stirred overnight at room temperature, and at 55° C. for 2 hours. The volatiles were removed by distillation in vacuo and the residue was neutralized with dilute hydrochloric acid, and extracted with ethyl acetate. The organic extract was washed with brine and dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound (0.070 g, 80%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.92 (d, 2H, J=9.0 Hz), 6.83 (d, 1H, J=2.1 Hz), 6.80 (d, 1H, J=2.1 Hz), 6.65 (d, 2H, J=9.0 Hz), 4.30 (s, 2H), 3.34 (s, 3H), 2.64 (q, 2H, J=7.6 Hz), 1.35(s, 6H), 1.23 (t, 3H, J=7.6 Hz).

Provenance & Evidence