Hydrochloric Acid → HCID 22241518, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of {2-methyl-6-[3-(quinolin-2-ylaminomethyl)-phenoxymethyl]-phenoxy}-acetonitrile (134 mg, 0.31 mmol, example 35a) in methanol (1 mL) is added THF (1 mL) followed by sodium hydroxide solution (0.2 mL, 10 N). The resulting mixture is warmed to 60° C. and stirred at this temperature for 3 h. The reaction mixture is then cooled to room temperature and acidified to ca. pH 5 with hydrochloric acid (1 mL, 2N), then extracted with ethyl acetate, washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 10% methanol in dichloromethane) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.10 (d, 1H), 7.80 (d, 1H), 7.68 (t, 2H), 7.40 (t, 1H), 7.25 (m, 2H), 7.04 (m, 3H), 6.90 (m, 3H), 6.6 (bs, 0.1H), 5.15 (s, 2H), 4.60 (d, 2H), 4.50 (s, 2H), 2.27 (s, 3H). MS (ESI) 429 (M+H)+.

Provenance & Evidence