Methyl iodide → 2-Methoxy-4-methylpyridine

HRID 1660716Notes

Reaction equation

HRID 1660716 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.I[CH3:10]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH3:10][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178428601HCID 178428601, compound

Product 1

HCID 142234722-Methoxy-4-methylpyridineYield 71%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2-hydroxy-4-methylpyridine (10 g, 92 mmol) in chloroform (350 mL) was added at room temperature silver carbonate (34.2 g, 124 mmol) and iodomethane (130 g, 920 mmol). The reaction mixture was stirred in the dark for 48 h, and then filtered through Celite and washed with ether. The filtrate was concentrated below 20° C., and the residue was purified by chromatography with pentane/ether (5:1) to afford 2-methoxy-4-methylpyridine as a colorless oil (8.0 g, 71%). 1H NMR (CDCl3) δ 8.02 (d, 1H, J=5.4 Hz), 6.69 (d, 1H, J=5.4 Hz), 6.55 (s, 1H), 3.91 (s, 3H), 2.28 (s, 3H); 13C NMR (CDCl3) δ 164.40, 149.72, 146.31, 118.21, 110.88, 53.17, 20.81. MS m/z (%): 123 (M+, 76), 122 (100).

Workup

  1. filtrationfiltered through Celite
  2. washwashed with ether
  3. concentrationThe filtrate was concentrated below 20° C.
  4. customthe residue was purified by chromatography with pentane/ether (5:1)

Sources & evidence

ORD record
ord-f1928b9f906649358daa0b04f393477b
Source dataset
uspto-grants-2011_10
Patent number
US08030300B2

Reaction notes

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