Isopropanol → HCID 14994263, compound

Participants

Reaction Steps

To a stirred solution of 1-amino-3,3-dimethyloxindole (7.35 g) and isopropanol (167 ml) was added 4-chloropyridine hydrochloride (8.15 g). The flask was flushed with nitrogen and fitted with a condensor and nitrogen inlet. The reaction mixture was heated at reflux for 9 hours. Upon cooling to room temperature, the reaction mixture was poured into dilute aqueous sodium bicarbonate. The product was extracted thrice with ethyl acetate and once with dichloromethane. The combined organic layers were washed with brine and dried (K2CO3). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, 2% Et3N/0-2% MeOH/ether) afforded 3.5 g (33%) of the desired product.

Provenance & Evidence