反应详情

A solution of 4-((bromoacetyl)amino)nitrobenzene (12.0 g, 46.3 mmol) and 2-fluoroaniline (11.0 g, 102 mmol) in anhydrous DMF (60 mL) was heated to 90°-100° C. for 2 days with stirring under N2. The solution was cooled, poured into 500 mL of ice-water, and then extracted with CH2Cl2 (200 mL). The organic layer was dried (MgSO4) and filtered, a small amount of silica gel was added to the CH2 Cl2 solution, and then the mixture was concentrated. Purification by chromatography, eluting with hexane-ethyl acetate (3:1), afforded 8.54 g (63.7%) of the title compound as yellow crystals, mp 150°-153° C.; 1H NMR (DMSO-d6) δ10.65 (s, 1H), 8.22 (d, J=9.2, 2H), 7.86 (d, J=9.2, 2H), 7.04 (ddd, J=9.6, J=8.4, J=1.6, 1H), 6.94 (dt, J=7.2, J=1.2, 1H), 6.65-6.61 (m, 2H), 5.80 (bs, 1H), 4.02 (s, 2H); 13C NMR (DMSO-d6) δ170.06, 150.91 (d, J=236), 144.99, 142.23, 136.31 (d, J=11.3), 124.98, 124.75 (d, J=3.5), 118.90, 116.36 (d, J=6.4), 114.44 (d, J=17.6), 112.17 (d, J=14.0), 46.79; MS (El, m/z) 289 (M+). Anal. Calcd for C14H12N3 O3F: C, 58.12; H, 4.18; N, 14.53. Found: C, 58.04; H, 4.20; N, 14.36.

1. temperatureThe solution was cooled
2. extractionextracted with CH2Cl2 (200 mL)
3. dry with materialThe organic layer was dried (MgSO4)
4. filtrationfiltered
5. additiona small amount of silica gel was added to the CH2 Cl2 solution
6. concentrationthe mixture was concentrated
7. customPurification by chromatography
8. washeluting with hexane-ethyl acetate (3:1)