Water → 6,7,8,9-tetrahydro-1H-benzo[g]indole

Participants

Reaction Conditions

Reaction Steps

To a suspension of lithium aluminium hydride (2.85 g, 75.0 mmol) in dry tetrahydrofuran (150 mL) was added 6,7,8,9-tetrahydro-1H-benz[g]indole-2,3-dione (3.018 g, 15.0 mmol) portionwise over 30 min. The green suspension was heated under reflux for 18 h and then cooled to 0° C. The suspension was treated with water (2.8 mL), 5 N aqueous sodium hydroxide (2.1 mL), and water (9.2 mL), and was stirred for an additional 1 h. The suspension was then filtered, the residue was washed with tetrahydrofuran, and the filtrate then concentrated in vacuo. The residue obtained was purified by column chromatography [SiO2; ethyl acetate-heptane (1:19)] and triturated with hexane to give the title indole (1.58 g, 62%) as a white solid: mp. 93–94° C. (lit. [Khim. Geterotsikl. Soedin., 1978, 14, 634] 89–90° C.); Found: C, 84.25; H, 7.65; N, 8.16%. C12H13N requires: C, 84.17; H, 7.65; N, 8.18%.

Provenance & Evidence