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

Participants

Reaction Steps

To a 250 ml round-bottomed flask equipped with condenser and N2 inlet were added 30.7 g (230 mmol) aluminum chloride, 150 ml carbon disulfide, and 3.8 ml (48 mmol) chloroacetyl chloride. To the stirring mixture was added 5.0 g (37 mmol) of oxindole portionwise over 15 minutes. The reaction was stirred a further 10 minutes, then refluxed 2 hours. The reaction was cooled, added to ice, stirred thoroughly, and the beige precipitate filtered, washed with water, and dried to afford 7.67 g (97%) of 5-chloroacetyloxindole. NMR (d, DMSO-d6): 3.40 (s, 2H), 5.05 (s, 2H), 6.8-7.9 (m, 3H).

Provenance & Evidence