2-ethyl-1H-indole → 2-ethyl-2,3-dihydro-1H-indole

Participants

Reaction Steps

0.66 g (4.2 mmol) 2-ethyl-1H-indole in 10 mL acetic acid were mixed with 1.3 g (20 mmol) sodium cyanoborohydride and stirred for one day at RT. The reaction mixture was evaporated down using the rotary evaporator, combined with 20 mL aqueous 4N hydrochloric acid and stirred for 1 h at RT. While cooling with ice 45 mL of an aqueous 4N sodium hydroxide solution were then added and the mixture was extracted with ethyl acetate. The organic phase was dried on sodium sulphate, filtered, evaporated down and the residue was dried in vacuo.

Provenance & Evidence