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

Participants

Reaction Steps

α-Chloroacetyl chloride (47.4 g) and 80.0 g of finely-ground anhydrous aluminum chloride were suspended in 100 ml of carbon bisulfide under ice-cooling. Oxindol (26.6 g) was added thereto with vigorous stirring and the mixture was refluxed for about 3 hours. Then the solvent was removed under reduced pressure, and the residue was poured into 1 l of ice-water and allowed to cool for a while. Crystals which precipitated were collected by filtration, washed successively with water, methanol, and diethyl ether, and dried to give 15 g of 5-(α-chloroacetyl)oxindol.

Provenance & Evidence