2-(2-Hydroxyethyl)pyridine → Pyridine, 2-(2-chloroethyl)-, hydrochloride

Participants

Reaction Steps

2-(2-hydroxyethyl)pyridine (5 g, 41 mmol) was dissolved in 10 mL of 1,2-dichloroethane, and thionyl chloride (9.67 g, 81 mmol) was added slowly at room temperature. The reaction mixture was stirred for one hour at room temperature and was then concentrated at reduced pressure. Methylene chloride (20 mL) was twice added to the concentrated residue and then removed under reduced pressure. The resulting concentrated residue was dried in vacuo to give 7.17 g (98.5%) of 2-(2-chloroethyl) pyridine·hydrochloride as a yellow solid: HRMS: calcd for C7 H8N1Cl1 142.0424, found 142.0400.

Provenance & Evidence