反应详情

温度

80 °C

Methyl 3-methyl-2-(3-(4-nitrophenyl)isoxazole-5-carboxamido)butanoate (2 g) was dissolved in EtOH (20 ml), THF (8 ml), and water (8 ml). Then ammonium chloride (925 mg) and Iron (756 mg) was added and refluxed at 80° C. for 3 h. The reaction mixture was cooled, filtered through celite and solvent removed under reduced pressure to get dark brown residue. Residue was taken in water and extracted with ethyl acetate, organic layer separated, dried over Na2SO4 and concentrated to get dark brown residue which was purified by silica gel column chromatography in 1:1 EtOAc:Pet ether to get yellow solid which was crystallized from methylene chloride/Pet ether to yield 1.2 g (65%) pale yellow solid. MS (ES+): m/z 318 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ 9.1 (d, 1H), 7.55 (d, 2H), 7.51 (s, 1H), 6.63 (d, 2H), 5.63 (bs, 1H), 4.27 (m, 1H), 3.65 (s, 3H), 2.19 (m, 1H), 0.94 (d, 6H).

1. temperatureThe reaction mixture was cooled
2. filtrationfiltered through celite and solvent
3. customremoved under reduced pressure
4. customto get dark brown residue
5. extractionextracted with ethyl acetate, organic layer
6. customseparated
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customto get dark brown residue which
10. customwas purified by silica gel column chromatography in 1:1 EtOAc
11. customPet ether to get yellow solid which
12. customwas crystallized from methylene chloride/Pet ether