反应详情

4-[2-(Pyridin-2-yloxy)ethoxy]aniline (4.50 g, 19.50 mmol) and 4-fluoro-3-nitrobenzoic acid (3.60 g, 19.50 mmol) were dissolved in ethanol (100 mL) and refluxed under nitrogen for 18 h. The reaction mixture was filtered and washed with cold ethanol (×2) to give 3-nitro-4-({4-[2-(pyridin-2-yloxy)ethoxy]phenyl}amino) benzoic acid as a reddish orange solid. 1H NMR (d6-DMSO, 400 MHz): δ 9.77 (brs, 1H), 8.64 (d, J=2.4 Hz, 1H), 8.18 (ddd, J=5.2, 2.0, 0.8 Hz, 1H), 7.88 (dd, J=9.6, 2.0 Hz, 1H), 7.73 (ddd, J=8.8, 6.8, 2.0 Hz, 1H), 7.29 (ddd, J=6.4, 3.2, 3.2 Hz, 1H), 7.08 (ddd, J=5.6, 3.2, 3.2 Hz, 1H), 7.01 (ddd, J=7.4, 5.2, 1.2 Hz, 1H), 6.97 (d, J=9.2 Hz, 1H), 6.87 (ddd, J=8.4, 0.8, 0.8 Hz, 1H), 4.60 (m, 2H), 4.37 (m, 2H), 4.15 (m, 2H). MS(ES+): m/z 396.45 (100) [MH+].

1. temperaturerefluxed under nitrogen for 18 h
2. filtrationThe reaction mixture was filtered
3. washwashed with cold ethanol (×2)