Aluminium lithium hydride → (5-Chloro-1-methyl-1H-indol-2-ylmethyl)methylamine

Participants

Reaction Steps

To an ice-cold solution of 5-chloro-1-methyl-1H-indole-2-carboxylic acid methylamide (2.12 g, 9.5 mmol) in THF (15 mL) was added lithium aluminum hydride (19 mL of a 1 M solution in THF, 19.0 mmol). Once the addition was complete, the resulting slurry was heated to reflux overnight. The mixture was cooled in an ice bath and carefully quenched by the consecutive addition of water (0.90 mL), 15% aqueous NaOH (0.90 mL) and water (2.5 mL). The resulting mixture was filtered through diatomaceous earth and the filtrate concentrated to give the title (2.00 g, quantitative) compound as an orange oil: 1H NMR (300 MHz, CDCl3) δ 7.51 (d, J=1.8 Hz, 1H), 7.25-1.14 (m, 2H), 6.32 (s, 1H), 3.86 (s, 2H), 3.73 (d, J=4.8 Hz, 3H), 2.49 (s, 3H).

Provenance & Evidence