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

HRID 1614106Notes

Reaction equation

HRID 1614106 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1>C(Cl)(Cl)Cl>[ClH:3].[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][CH2:6][Cl:3]

Participants

4

Reactant 2

HCID 76752-(2-Hydroxyethyl)pyridineHCID 24386Thionyl Chloride

Product 1

HCID 199467Pyridine, 2-(2-chloroethyl)-, hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thionyl chloride (SOCl2, 6.2 ml) in chloroform (15 ml) was added dropwise to an ice chilled solution of 2-(2-hydroxyethyl)pyridine (Aldrich, 10 g, 81 mmol in chloroform (10 ml. After addition was complete, the reaction mixture was stirred for 15 hours. The solvent and excess thionyl chloride were removed on a vacuum rotary evaporator followed by exposure to high vacuum (90 minutes, 0.5 mm Hg, 80° C.) Recrystallization of the crude brown solid from isopropanol-isopropyl ether yielded 10.8 g of pure 2-(2-pyridinyl)ethyl chloride hydrochloride (mp. 124°-125° C., lit. mp., about 120° C., Gump et al., U.S. Pat. No. 2,533,243; Chem. Abstr., 1950, 45, p. 4271c) as light tan beads.

Workup

  1. additionAfter addition
  2. customThe solvent and excess thionyl chloride were removed on a vacuum rotary evaporator
  3. customfollowed by exposure to high vacuum (90 minutes, 0.5 mm Hg, 80° C.) Recrystallization of the crude brown solid from isopropanol-isopropyl ether

Sources & evidence

ORD record
ord-17be4a11b34c40b4a6d5b975b13adad3
Source dataset
uspto-grants-1993_03
Patent number
USRE034201

Reaction notes

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