Dimethylformamide → 5-nitro-1H-indol-1-amine

Participants

Reaction Conditions

Reaction Steps

NaH (60%, 421.5 mmol) is added portion-wise to a solution of 5-nitro-1H-indole (28.1 mmol) in anhydrous DMF (80 mL) at 0° C. and the mixture is stirred at 0° C. under N2 for 10 min. HOSA (140.5 mmol) is added portion-wise for 30 minutes and the mixture is stirred at 0° C. for 2 h. The reaction is quenched with water. Additional water (250 mL) is added and the mixture is extracted with EtOAc (3×100 mL). The combined organic layer is washed with water (2×30 mL), brine (30 mL), dried (Na2SO4), filtered and concentrated. The residue is washed with heptane (2×20 mL) and recrystallized from EtOAc to afford 5-nitro-indole-1-ylamine (4.84 g, 97%) as a solid. MS: 178 (M+H); 1H NMR (300 MHz, CDCl3): δ 4.93(br, 2N—H), 6.62(d, H), 7.30(d, H), 7.52(d, H), 8.17(d, H), 8.58 (s, H).

Provenance & Evidence