反应详情

To a solution of (E)-3-methyl-4-nitrobenzaldehyde oxime (1.0 equiv.) in dimethylformamide, N-chlorosuccinimide (1.2 equiv.) was added in 3 portions over the period of 1 hr and the reaction mixture was stirred at r.t. for 5 hours. DMF was evaporated and the residue was diluted with EtOAc. The organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 5% ethyl acetate in petroleum ether (60-80), to provide the title compound as a creamish solid (78%); 1H NMR (300 MHz, DMSO-d6) δ: 2.55 (s, 3H), 7.81-7.84 (d, J=8.7 Hz, 2H), 7.86 (s, 1H), 8.04-8.07 (d, J=8.4 Hz, 1H), 12.86 (s, 1H); IR (KBr) 3320, 3105, 2925, 1607, 1583, 1521, 1440, 1387, 1358, 1310, 1259, 1183, 1010, 860 cm−1.

1. customDMF was evaporated
2. additionthe residue was diluted with EtOAc
3. washThe organic layer was washed with water, brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography on silica gel
8. washeluting with 5% ethyl acetate in petroleum ether (60-80)