Water → 2,3-dihydro-1H-indol-1-amine

Participants

Reaction Steps

A solution of 1-nitroso-2,3-dihydro-1H-indole (5.27 g, 35.6 mmol) in tetrahydrofuran (35 ml) was added dropwise to a refluxing slurry of lithium aluminium hydride (2.98 g, 78.5 mmol) in tetrahydrofuran (100 ml). After 1 hour the mixture was cooled in an ice bath and water (3 ml) carefully added. 2M sodium hydroxide (6 ml) followed by water (6 ml) were added and the mixture heated to reflux for 30 minutes. After cooling to room temperature the precipitate formed was filtered off. The filtrate obtained was evaporated to dryness to yield 2,3-dihydro-indol-1-ylamine as a red/brown oil (4.216 g), which was used for the next step without further purification.

Provenance & Evidence