Hydrochloric Acid → 3-(Methylsulfanyl)-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

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Reaction Steps

Following the procedure described in PCT Published Patent Application, WO 99/10325, a solution of 4-cyanoaniline (10 g, 84 mmol) in dry dichloromethane (200 mL) under nitrogen was cooled to −78° C. To this stirred solution was added a solution of t-butylhypochlorite (10.9 mL, 84 mmol) in dry dichloromethane (20 mL). The resulting solution was stirred for 10 minutes. A solution of ethyl methylthioacetate (10.9 mL, 84 mmol) in dichloromethane (20 mL) was added dropwise. After 1 hour, triethylamine (12 mL, 86 mmol) was added dropwise to the solution and the resulting reaction mixture was allowed to warm to ambient temperature over 1 hour. The reaction mixture was washed with water, brine, dried (Na2SO4) and concentrated to afford an orange oil. This oil was dissolved in ether (200 mL) and treated with 2N HCl (15 mL). The reaction mixture was stirred vigorously at room temperature for 18 hours. The resulting solid was collected by filtration, washed with ether, and dried in vacuo to afford 5-cyano-3-methylthioindolin-2-one as a solid (11 g).

Provenance & Evidence