Sodium Hydroxide → HCID 178507365, compound

Participants

Reaction Steps

A mixture of 3-(1-naphthylsulfanyl)-5-nitro-1H-indazole (5.50 g, 17.11 mmol) and 3-chloroperoxybenzoic acid (17.91 g, 103.80 mmol) in CHCl3 was stirred at room temperature for 4 hours, diluted with EtOAc, washed sequentially with Na2SO3 solution, water and brine, dried over Na2SO4, and concentrated in vacuo to give a residue. A mixture of this residue, tin mossy (15.79 g, 133.01 mmol) in MeOH and conc. hydrochloric acid was heated at 60° C., cooled to room temperature, diluted with CH2Cl2 and basified with NaOH. The phases were separated. The aqueous phase was extracted with CH2Cl2. The organic phase and the extracts were combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue was purified chromatographically, to provide the title compound, 2.50 g, (45% overall yield), characterized by HNMR and mass spectral analyses. MS (ES+) m/e 324 (MH+).

Provenance & Evidence