1,2,3,4-Tetrahydro-1-nitrosoquinoline → 1,2,3,4-Tetrahydroquinolin-1-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-nitroso-1,2,3,4-tetrahydroquinoline (10.0 g, 61.66 mmol) in 60 mL dry THF was added dropwise to a refluxing suspension of LiAlH4 (4.26 g, 112.21 mmol) in 130 mL THF. The reaction was allowed to reflux for 1 hour, cooled to 0° C., and then quenched by the dropwise addition of Rochelle's salt solution. The resulting precipitate was diluted with THF and filtered. The filtrate was then concentrated under reduced pressure, then purified by flash chromatography to give the product (4.83 g, 52.9%) as a white solid. 1H-NMR (300 MHz, CDCl3): δ 7.12 (m, 2H), 6.95 (d, 1H), 6.69 (m, 1H), 3.32 (m, 2H), 2.75 (t, 2H), 2.04 (dt, 2H) ppm; MS m/z calculated for C9H13NO (M+H): 149.1. Found 149.1 (M+H, ESI+).

Provenance & Evidence