2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(Tert-butyl)-6-nitro-1H-indole

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Reaction Steps

To a solution of 2-tert-butyl-6-nitroindoline (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ (6.9 g, 30 mmol) at room temperature. The mixture was heated at reflux for 2.5 h before being filtered and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%). 1 H NMR (300 MHz, CDCl3) δ 8.30(br. s, 1 H), 8.29(s, 1 H), 8.00(dd, J=2.1, 8.7 Hz, 1 H), 7.53(d, J=9.3 Hz, 1 H), 6.38(s, 1 H), 1.43(s, 9 H).

Provenance & Evidence