Toluene → HCID 54738210, compound

Participants

Reaction Steps

Potassium bis(trimethylsilyl)amide in toluene (0.5M, 10.8 ml, 5.4mmol) was added dropwise to a solution of methyl [3-(2-pyridyloxy)phenyl]acetate (0.52 g, 2.14 mmol) and methyl 2-amino-4-chlorobenzoate (0.43 g, 2.32 mmol) in dry THF (30 ml). The reaction mixture was stirred at room temperature for 3 1hours then methanol (10 ml) was added. The solution was concentrated in vacuo, the residue was dissolved in 0.5M sodium hydroxide (25 ml) and washed with diethyl ether (2×25 ml). The aqueous phase was acidified with 5M hydrochloric acid. The resultant precipitate was collected and recrystallised from dimethylformamide/water to afford the title compound as a pale cream solid (0.463 g, 59%). A further recrystallisation from propan-2-ol gave analytically pure material; m.p. 269°-271° C. (from propan-2-ol) (Found: C, 65.92;H, 3.71;N, 7.59. C20H13ClN2O3 requires C, 65.85;H, 3.71;N, 7.68%); δH (360 MHz, DMSO-d6) 7.03-7.14 (4H, m, ArH), 7.23 (1H, dt, J 2, 8.5 Hz, ArH), 7.32 (1H, d, J 2 Hz, ArH), 7.43 (1H, t, J 8 Hz, 5'-H), 7.85 (1H, m, ArH), 7.94 (1H, d, J 8.7 Hz, 5-H), 8.18 (1H, dd, J 5, 2 Hz, 6"-H), 10.46 (1H, br s, OH), 11.55 (1H, br s, NH); m/z 364 (M+).

Provenance & Evidence