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

HRID 344683Notes

Reaction equation

HRID 344683 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-0d93e52a4142403e87c604ef1fd66b13
Source dataset
uspto-grants-1991_10
Patent number
US05053411

Reaction notes

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