反应详情

To a solution of 2-fluoro-6-nitro-3-phenoxyaniline (260 mg, 1.05 mmol) in methanol (20 ml) was added tin(II)chloride (1.18 g, 5.24 mmol). The reaction was heated to reflux overnight and then cooled to rt. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (50 mL). The solution was poured into an aqueous saturated sodium bicarbonate solution (150 mL), causing a precipitate to crash out. The mixture was filtered using ethyl acetate to rinse. The filtrate was washed with water and brine, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography using 0-70% ethyl acetate/hexane to yield the desired product (195 mg, 85%) 1H NMR (300 MHz, DMSO-d6) 7.22-7.31 (m, 2H), 6.94-7.01 (m, 1H), 6.82 (d, J=7.8 Hz, 2H), 6.31 (dd, J=8.5, 1.5 Hz, 1H), 6.20 (dd, J=8.5, 8.5 Hz, 1H); ES-MS m/z 219.3 (MH)+; HPLC RT (Method A) 2.40 min.

1. temperatureThe reaction was heated
2. temperatureto reflux overnight
3. concentrationThe mixture was concentrated under reduced pressure
4. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
5. additionThe solution was poured into an aqueous saturated sodium bicarbonate solution (150 mL)
6. filtrationThe mixture was filtered
7. washto rinse
8. washThe filtrate was washed with water and brine
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by silica gel chromatography