Thionyl Chloride → 3-(1-Chloroethyl)-isoquinoline

Participants

Reaction Conditions

Reaction Steps

3-(1-Hydroxyethyl)-isoquinoline (1.32 g, 7.6 mmole) is dissolved in 20 ml dichloromethane in a 100 ml one neck round bottom flask under nitrogen. The solution is cooled to 0° C., is treated dropwise with thionyl chloride (835 μl, 11.4 mmole), and is stirred 3 h at 0° C. followed by 1 h at room temperature. The mixture is recooled to 0° C., is quenched with 50 ml saturated sodium bicarbonate, and the layers are separated. The aqueous layer is extracted with 3×25 ml dichloromethane and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to a pale amber oil. The crude material is chromatographed over 60 g silica gel (230-400 mesh), eluting with 20% acetone/hexane, while collecting 9 ml fractions. Fractions 17-26 are combined and concentrated to afford 1.39 g (95%) of 3-(1-chloroethyl)-isoquinoline as a yellow oil.

Provenance & Evidence