反应详情

To a stirred solution of 4.95 g (25.1 mmol) of 5-chloroisatoic anhydride in 80 mL of dry N,N-dimethylformamide (DMF) was added 5.15 g (48.6 mmol) of powdered sodium carbonate forming a suspension. The suspension was then treated with 2.00 mL (4.86 g; 32.1 mmol) of iodomethane. The resulting suspension was stirred for 13 hours, then it was poured into 300 mL of water with vigorous stirring. After 2-3 minutes the resulting precipitate was filtered, and washed with 200 mL of water. The filter cake was dissolved in 200 mL of dichloromethane and this solution was dried (Na2SO4). The solution was concentrated in vacuo and the residue triturated with ethyl acetate-hexane (1:3). The solid was filtered, washed with ethyl acetate-hexane (1:3), and finally hexane. The solid was dried in vacuo to give 3.90 g (73%) of the title compound as a pale yellow solid. 1H NMR (300 MHz, DMSO-D6) d 3.42 (s, 3 H), 7.44 (d, 1 H), 7.85 (d, 1 H0, 7.83, (d, 1 H), 7.92 (d, 1 H). MS (Cl Mode) m/z 212 (M+H, 100%), 240 (M+29, 8%). HPLC analysis showed a single peak.

1. filtrationAfter 2-3 minutes the resulting precipitate was filtered
2. washwashed with 200 mL of water
3. dissolutionThe filter cake was dissolved in 200 mL of dichloromethane
4. dry with materialthis solution was dried (Na2SO4)
5. concentrationThe solution was concentrated in vacuo
6. customthe residue triturated with ethyl acetate-hexane (1:3)
7. filtrationThe solid was filtered
8. washwashed with ethyl acetate-hexane (1:3), and finally hexane
9. customThe solid was dried in vacuo