Water → 2-(7-nitro-1H-indol-3-yl)ethan-1-amine

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Reaction Steps

Dissolve in a 500 mL round bottom flask equipped with magnetic stirring, and a nitrogen inlet, (7-nitro-1H-indol-3-yl)-acetonitrile (5.27 g, 26 mmol) in dry tetrahydrofuran (150 mL). Treat the solution with 1M BH3:THF (55 mL, 55 mmol) and stir at room temperature. After 20 hours, quench the reaction by the cautious dropwise addition of water (9 mL) and stir until foaming and gas evolution has stopped. Concentrate the mixture to dryness in vacuo, redissolve in 1 N HCl (300 ml) and extracte with ethyl acetate. Basify the aqueous phase 5 N NaOH and extract with ethyl acetate. Pool the ethyl acetate extracts and dry over sodium sulfate and concentrate in vacuo to give the title compound as an orange-brown solid: 1H NMR (400 MHz, dmso-d6): 11.66 (br s, 1H) 8.07 (t, 2H, J=7.6 Hz), 7.32 (s, 1H), 7.20 (t, 1H, J=8.0 Hz) 2.79-2.83 (m, 4H), MS (APCI): m/e 189.0 (M−NH2).

Provenance & Evidence