Methyl iodide → 2-Methoxy-6-methylpyridine

HRID 900065Notes

Reaction equation

HRID 900065 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.I[CH3:10]>C(=O)([O-])[O-].[Ag+2].C(Cl)(Cl)Cl>[CH3:10][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178425782HCID 178425782, compound

Product 1

HCID 53247732-Methoxy-6-methylpyridineYield 80.8%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 2-hydroxy-6-methylpyridine (6.85 g, 62.8 mmol), silver carbonate (22.5 g, 81.6 mmol), iodomethane (39.1 mL, 628 mmol) and chloroform (200 mL) was stirred at ambient temperature for 40 h in the dark. The reaction mixture was filtered through celite. The collected solid was washed with ether. The combined filtrates were concentrated in vacuo to give a liquid (6.25 g), which was identical to the product from Part A.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washThe collected solid was washed with ether
  3. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-c64f77ab5c5949e0b5cc7d9537990ea8
Source dataset
uspto-grants-2008_04
Patent number
US07358252B2

Reaction notes

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