反应详情

To a solution of 16.3 g (0.1 mol) of 2-amino-5-nitrobenzonitrile in 200 ml of CH2Cl2 at 0° C. was added 21 ml (0.15 mol) of triethyl amine followed by 0.3 g of DMAP and 11.71 g (0.11 mol) of butyryl chloride. The reaction mixure was warmed to room temperature and then heated over night at 50° C. The solution was washed with 1N HCl (1×20 ml), water (1×20 ml), saturated NaHCO3 (2×20 ml) and brine (1×20 ml) and dried over MgSO4. The solution was filtered and concentrated in vacuo. The residue was dissolved in 200 ml of MeOH to which was added 44 ml (0.22 mol) of 5M NaOH solution followed by the dropwise addition of 25 ml (0.22 mol) 30% H2O2 and 50 ml of water. The mixture was refluxed for 4 hours, cooled and filtered. The filtrate was acidified with 1N HCl and the resulting precipitate recovered by filtration. The residue was recrystalized from MeOH to give 8.3 g (0.036 mol) of pale brown fluffy crystals. 1H-NMR (CDCl3): 1.10 (t, 3H, J=7.4 Hz), 1.93 (m, 2H), 2.79 (3 line m, 2H, J=7.3 Hz), 7.80 (d, 1H, J=8.9 Hz), 8.55 (dd, 1H, J=2.5, 8.8 Hz), 9.14 (bs, 1H).

1. customThe reaction
2. temperatureheated over night at 50° C
3. washThe solution was washed with 1N HCl (1×20 ml), water (1×20 ml), saturated NaHCO3 (2×20 ml) and brine (1×20 ml)
4. dry with materialdried over MgSO4
5. filtrationThe solution was filtered
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in 200 ml of MeOH to which
8. temperatureThe mixture was refluxed for 4 hours
9. temperaturecooled
10. filtrationfiltered
11. filtrationthe resulting precipitate recovered by filtration
12. customThe residue was recrystalized from MeOH