Ethyl Acetate → 2-(6-fluoro-1H-indol-3-yl)ethanamine

Participants

Reaction Conditions

Reaction Steps

Aluminum lithium hydride (1.36 g) was suspended in tetrahydrofuran (72 ml), 6-fluoro-3-[(E)-2-nitrovinyl]-1H-indole (1.48 g) was dissolved in tetrahydrofuran (20 ml) and added dropwise under ice-cooling, and the mixture was stirred at 60° C. for 1 hr. Under ice-cooling, excess aluminum lithium hydride was decomposed with ice water, ethyl acetate was added, and the mixture was filtered through a celite (trademark) filter. A 1N aqueous sodium hydroxide solution was added to the filtrate, pH was adjusted to not less than 11, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a brown oil. The oil was purified by amine coating silica gel column chromatography (elution solvent:ethyl acetate-ethyl acetate-methanol (10:1)) to give 6-fluorotryptamine (1.24 g, yield 97%).

Provenance & Evidence