Diethyl Ether → 2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride

HRID 35472Notes

Reaction equation

HRID 35472 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10]O)[C:4]=1[CH3:12].S(Cl)([Cl:15])=O.CCOCC>C(Cl)Cl>[ClH:15].[Cl:15][CH2:10][C:5]1[C:4]([CH3:12])=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 7378233,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

Product 1

HCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

75.8 g of 4-methoxy-3,5-dimethyl-2-pyridylmethanol dissolved in 200 ml of methylene chloride are added dropwise at 0° to 38 ml of thionyl chloride in 400 ml of methylene chloride. After stirring at room temperature for 16 hours 1800 ml of ether are added dropwise thereto while cooling and the mixture is stirred further at room temperature for 2 hours. The precipitated crystals are filtered off under suction and washed with ether. There is obtained 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride of melting point 130°-131°.

Workup

  1. additionare added dropwise
  2. temperaturewhile cooling
  3. filtrationThe precipitated crystals are filtered off under suction
  4. washwashed with ether

Sources & evidence

ORD record
ord-dc9c0c9fe8b741c7b7bf37882c0aa27e
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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