Toluene → 2-(1-Chloroethyl)-4-methoxy-pyridine hydrochloride

HRID 1789058Notes

Reaction equation

HRID 1789058 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH:13](O)[CH3:14])[CH:8]=1.C1(C)C=CC=CC=1>ClCCl>[ClH:3].[Cl:3][CH:13]([C:9]1[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=[CH:11][N:10]=1)[CH3:14]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 201895551-(4-Methoxypyridin-2-YL)ethan-1-OL

Product 1

HCID 201895902-(1-Chloroethyl)-4-methoxy-pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

36 ml of thionyl chloride are added dropwise to a cooled suspension of 57 g of (±)-1-[4-methoxy-2-pyridyl]ethanol in 400 ml of dichloromethane, in such a way that the internal temperature does not exceed 15° C. The mixture is then heated under reflux for 2.5 h, treated with 300 ml of toluene and concentrated to 150 ml. The reaction product which has precipitated is filtered off with suction and rinsed with cold toluene and petroleum ether. This gives 76.4 g (98.2%) of the title compound of m.p. 113°-116° C.

Workup

  1. customdoes not exceed 15° C
  2. temperatureThe mixture is then heated
  3. temperatureunder reflux for 2.5 h
  4. concentrationconcentrated to 150 ml
  5. customThe reaction product which has precipitated
  6. filtrationis filtered off with suction
  7. washrinsed with cold toluene and petroleum ether

Sources & evidence

ORD record
ord-d9e9a77157924c8592aec16db23141ed
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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