Sodium Hydroxide → HCID 11210335, compound

Participants

Reaction Steps

To a suspension of 370 mg (2.3 mmole) 4-nitro-1H-indole in 10 mL toluene was added 5 mL 4 M sodium hydroxide and 50 mg tetra-n-butyl ammonium hydrogen sulfate. Solid naphthalene-1-sulfonyl chloride (533 mg, 2.35 mmole) was added in one portion. The reaction mixture was stirred at room temperature for 0.25 hr. The mixture was diluted with 5 mL water and extracted with 25 mL ethyl ether. The organic phase was washed with 5 mL water, 5 mL saturated sodium chloride, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from ether/hexane to provide 1-(naphthalene-1-sulfonyl)-4-nitro-1H-indole as light yellow crystals, 779 mg, m.p. 156-157° C.

Provenance & Evidence