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

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).

1. waitAfter 1 hour
2. customthe resulting reaction mixture
3. washThe reaction mixture was washed with water, brine
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. customto afford an orange oil
7. stirringThe reaction mixture was stirred vigorously at room temperature for 18 hours
8. filtrationThe resulting solid was collected by filtration
9. washwashed with ether
10. customdried in vacuo

ORD record

ord-a39d03e5f33a4f2f80de6097894e8402

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105563B2