Diethyl Ether → 2-(Chloromethyl)-4-methoxy-5-methylpyridine hydrochloride

HRID 979869Notes

Reaction equation

HRID 979869 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10]O)[CH:4]=1.S(Cl)([Cl:14])=O.CCOCC>C(Cl)Cl>[ClH:14].[Cl:14][CH2:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 15163463(4-Methoxy-5-methylpyridin-2-yl)methanol

Product 1

HCID 221514312-(Chloromethyl)-4-methoxy-5-methylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

28.1 g of 4-methoxy-5-methyl-2-pyridylmethanol, dissolved in 180 ml of methylene chloride, were added dropwise at 0° to 17 ml of thionyl chloride in 360 ml of methylene chloride. After stirring at room temperature for 16 hours 1400 ml of ether were added dropwise thereto while cooling and the mixture was stirred at room temperature for a further 2 hours. The separated crystals were filtered off under suction and washed with ether. There was obtained 2-(chloromethyl)-4-methoxy-5-methylpyridine hydrochloride of melting point 149°-151°.

Workup

  1. additionwere added dropwise
  2. temperaturewhile cooling
  3. filtrationThe separated crystals were filtered off under suction
  4. washwashed with ether

Sources & evidence

ORD record
ord-9105b191e98344bb8a771c7a62363c38
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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