Chloroform → 3-(5-Cyano-2-nitrophenyl)-5-(3-cyanophenyl)isoxazole

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3-(5-Cyano-2-nitrophenyl)-5-(3-cyanophenyl)isoxazole (501) was prepared from bromoisoxazole 49j as light yellow crystals (0.18 g, 24%): mp 225-227° C. (CHCl3); 1H NMR δ 8.48 (s, 1H), 8.45 (s, 1H), 8.35 (m, 2H), 8.25 (d, J=7.7 Hz, 1H), 8.05 (d, J=7.7 Hz, 1H), 7.82 (t, J=7.7 Hz, 1H), 7.70 (s, 1H); HPLC (Method B) tR 6.67 min (100 area % at 265 nm). Anal. (C17H8N4O3) C, H, N. 3-(5-Cyano-2-methoxyphenyl)-5-(3-cyanophenyl)isoxazole (50m) was prepared from bromoisoxazole 49k as light yellow crystals (1.41 g, 43%): mp 241-243° C. (CH2Cl2); 1H NMR δ 8.49 (s, 1H), 8.26 (m, 2H), 8.00 (br s, 2H), 7.78 (br s, 1H), 7.68 (br s, 1H), 7.42 (s, 1H); HPLC (Method B) tR 7.36 min (97.8 area % at 265 nm). Anal. (C18H11N3O2) C, H, N. 3-(2-Chloro-5-cyanophenyl)-5-(4-cyanophenyl)isoxazole (53j) was prepared by the general method for nitriles 50 above from bromoisoxazole 53i (1.90 g, 5.28 mmol). The crude product was purified by column chromatography (CHCl3). Purified fractions were evaporated. The residue was suspended in ether and filtered off to give a pale yellow solid (0.44 g, 27%); mp 257-259° C.; 1H NMR δ 8.29 (d, J=2.1 Hz, 1H), 8.17 (d, J=8.4 Hz, 2H), 8.08 (m, 3H), 7.95 (d, J=8.4 Hz, 1H), 7.80 (s, 1H); HPLC (Method B) tR 7.55 min (92.3 area % at 265 nm). Anal. (C17H8ClN3O.0.2H2O) C, H, N.

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