Chloroacetonitrile → HCID 605506, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture containing 50 g of 5-methoxy-l,3-dimethyloxindole, 10.57 g of Aliquat 366 in 375 ml of toluene and 100 ml of 50% NaOH was added dropwise under nitrogen, a solution containing 21.73 g of chloroacetonitrile in 125 ml of toluene over 30 min. A slightly exothermic reaction ensued (50° C.). The reaction mixture was stirred for another 10 minutes, and then cooled to 10° C. To this cooled reaction mixture was added 400 ml of ice-cold water. The reaction mixture was transferred to a separatory funnel. The layers were separated and the organic layer was extracted with 3N HCl (2×250 ml) and water (1×250 ml). The toluene extract was concentrated under reduced pressure and the resultant dark oil was filtered through silica gel (500 g) eluting with 3% methanol-methylene chloride mixture. The eluate (2 L) was concentrated to give the target compound as an oil (54.61 g; 91% yield) which slowly crystallized upon seeding. This material was sufficiently pure and was reduced to (±)-1,3-dimethyl-5-methoxy-oxindolylethylamine without further purification. A small sample of (±)-cyanomethyl-5-methoxy-1,3-dimethyloxindole was recrystallized from isopropyl ether, m.p.=75.5°-76° C. (lit: 75°-76° C.).

Provenance & Evidence