反应详情

To a stirred solution of isatoic anhydride (100 g) and propyl iodide (66 ml) in dimethylfomamide (600 ml) at 0° C., under nitrogen, was added sodium hydride (28 g of a 55% dispersion in mineral oil) portionwise. The mixture was allowed to warm to room temperature and stirred for 18 h. The solvent was then removed in vacuo and the residue partitioned between ethyl acetate (1000 ml) and water (500 ml). The organic phase was separated, washed with brine (2×500 ml), dried (MgSO4) and evaporated. The residue was triturated with anhydrous diethyl ether to give the title compound (57 g). 1H NMR (360 MHz, CDCl3) δ1.06 (3H, t, J=7.5 Hz), 1.75-1.86 (2H, m), 4.01-4.05 (2H, m), 7.17 (1H, d, J=8.5 Hz), 7.26-7.32 (1H, m), 7.73-7.78 (1H, m), 8.17 (1H, dd, J=7.9 and 1.7 Hz). MS (CI) m/e 205 [MH]+.

1. customThe solvent was then removed in vacuo
2. customthe residue partitioned between ethyl acetate (1000 ml) and water (500 ml)
3. customThe organic phase was separated
4. washwashed with brine (2×500 ml)
5. dry with materialdried (MgSO4)
6. customevaporated
7. customThe residue was triturated with anhydrous diethyl ether