Hydrochloric Acid → 3-(Chloromethyl)-2-methoxypyridine--hydrogen chloride (1/1)

HRID 1282283Notes

Reaction equation

HRID 1282283 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[C:12]([CH2:13]O)=[CH:11][CH:10]=[CH:9][N:8]=1.[ClH:15]>C(Cl)Cl>[ClH:3].[CH3:5][O:6][C:7]1[C:12]([CH2:13][Cl:15])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 10630565(2-Methoxypyridin-3-yl)methanol

Product 1

HCID 184240653-(Chloromethyl)-2-methoxypyridine--hydrogen chloride (1/1)Yield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

51 ml of thionyl chloride (696.67 mmol) were added dropwise to 17 g of 2-methoxy-3-picolyl alcohol.HCl (96.76 mmol) suspended in 60 ml of DCM, the solution was stirred at room temperature for 1 h, the solvent and excess thionyl chloride were removed under reduced pressure, and the residue was codistilled 4 times with methanol under reduced pressure and subsequently extracted by stirring with ether. 15.2 g of is 2-methoxy-3-picolyl chloride hydrochloride (81%) were obtained as a white crystalline salt.

Workup

  1. customthe solvent and excess thionyl chloride were removed under reduced pressure
  2. extractionsubsequently extracted
  3. stirringby stirring with ether

Sources & evidence

ORD record
ord-9940ffdcdbe34c05b56d73fd6bbd2c25
Source dataset
uspto-grants-2002_09
Patent number
US06455671B1

Reaction notes

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