反应详情

A solution of 5-cyano-3-methylthiooxindole (6.0 g, 29 mmol) in THF (100 mL) was stirred at room temperature and a saturated aqueous solution of NH4Cl (100 mL) added followed by activated zinc (25 g, 0.38 mol). The resulting mixture was stirred for 18 hours. The mixture was filtered through a pad of diatomaceous earth and the pad washed with THF (20 mL). The organic phase was separated, dried over anhydrous MgSO4 and the solvent evaporated to leave a tan solid. Trituration of this solid with diethyl ether gave 5-cyanooxindole a white solid, (4.1 g, 88%). 1H NMR (DMSO-d6) δ7.63 (d, 1H, J=8.4 Hz), 7.62 (s, 1H), 6.93 (d, 1H, J=8.4 Hz), 3.55 (s, 2H). MS (−ve ES) 157 (100), (M−H)

1. filtrationThe mixture was filtered through a pad of diatomaceous earth
2. washthe pad washed with THF (20 mL)
3. customThe organic phase was separated
4. dry with materialdried over anhydrous MgSO4
5. customthe solvent evaporated
6. customto leave a tan solid