Methyl iodide → 4-Chloro-2-methoxypyridine

HRID 2361640Notes

Reaction equation

HRID 2361640 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[CH:3]=1.[CH3:9]I>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 178516186HCID 178516186, compound

Product 1

HCID 226385104-Chloro-2-methoxypyridineYield 58.3%

Procedure

4-Chloro-2-hydroxy-pyridine (247 mg, 1.91 mmol), Ag2CO3 (1.58 g, 5.74 mmol) and MeI (0.13 ml, 2.11 mmol) were heated in a sealed tube at 50° C. for 16 hours and then filtered through celite and concentrated at reduced pressure. The residue was purified by FCC (Pentane/Diethyl ether with gradient, 99:1 to 95:5) to provide the title compound as colourless oil (160 mg, 58%).

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated at reduced pressure
  3. customThe residue was purified by FCC (Pentane/Diethyl ether with gradient, 99:1 to 95:5)

Sources & evidence

ORD record
ord-d80ddcccaf954eda99cdc4ff1490ad02
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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