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

HRID 703167Notes

Reaction equation

HRID 703167 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, were 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 were added dropwise thereto while cooling and the mixture was stirred at room temperature for a further 2 hours. The precipitated crystals were filtered off under suction and washed with ether. There was obtained 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride of melting point 130-131° .

Workup

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

Sources & evidence

ORD record
ord-cecc1d11b1374bafa728c5b997de29d7
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

Loading…