Chloroacetyl chloride → 5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

Participants

Reaction Steps

The following reagents were combined in the order listed under nitrogen at room temperature: aluminum chloride (17 g, 0.130 moles), carbon disulfide (40 mL), chloroacetyl chloride (3.01 g, 0.027 moles), and oxindole (2.73 g, 0.021 moles). The reaction mixture was warmed to reflux and stirring continued at this temperature for 3 h. The reaction was cooled to room temperature and the liquid was carefully decanted off. Ice water was added dropwise to the remaining residue under nitrogen (slowly and carefully). Addition of water was ceased when a total of 50 mL had been added and the reaction was stirred for 1 h at room temperature. The tan solid was collected by filtration, washed 3 times with water and dried in vacuo at 72° C. to give a light tan solid (3.4 g, 79% yield). 1H NMR (DMSO-d6) δ3.62 (s, 2H); 5.15 (s, 2H); 6.96 (d, 1H); 7.84 (s, 1H); 7.91 (d, 2H); 10.84 (bs, 1H). APCI-MS m/z 208 (M−H).

Provenance & Evidence