Water → 7-Bromo-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

A solution of 7-bromoquinoline (J. Amer. Chem. Soc., 1947, 69, 705) (362 mg, 1.74 mmol) in glacial acetic acid (10 ml) was treated portion-wise with sodium cyanoborohydride (437 mg, 7.0 mmol) under argon at room temperature. After 18 h at this temperature, the mixture was cooled in an ice bath and to it was added water (35 ml) and 50% aq. sodium hydroxide until pH 14 was attained. The mixture was extracted with dichloromethane and the organic phase washed with saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo to a residue which was purified by column chromatography over silica gel eluting with a gradient of methanol/dichloromethane to give the title compound (D15) (168 mg, 46%). MH+ 212/214.

Provenance & Evidence