Acetic Acid → 1,3-Dihydro-5-(phenylthio)-2H-pyrrolo[2,3-c]pyridin-2-one

Participants

Reaction Steps

A solution of t-butyl (3-nitro-6-phenylthio-2-pyridyl)acetate (1.04 g, 3.0 mmol) in glacial acetic acid containing iron powder (600 mg, 10.7 mmol) was heated at reflux for 5 hours. After cooling to room temperature, the mixture was poured into ice/water and extracted with chloroform. The combined chloroform extracts were washed with brine, dried (MgSO4) and concentrated to leave 5-phenylthio-6-azaoxindole as a light yellow solid (560 mg, 77%); m.p. 186°-189° C.

Provenance & Evidence