Methyl iodide → 2,6-Dichloro-3-methoxypyridine

HRID 1776793Notes

Reaction equation

HRID 1776793 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[Cl:1][C:2]1[C:7]([O:8][CH3:10])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1043172,6-Dichloropyridin-3-ol

Product 1

HCID 717433362,6-Dichloro-3-methoxypyridineYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,6-dichloropyridin-3-ol (16.3 g, 0.1 mol) and K2CO3 (41.4 g, 0.3 mol) in DMF (200 mL) were added MeI (21.3 g, 0.15 mol). The mixture was allowed to stir at 80° C. for 2 hours. The mixture was then diluted with water (200 mL) and extracted with EtOAc (200 mL×3). The organic layer was washed with brine (200 mL×3), dried over Na2SO4, filtered and the solvent was concentrated in vacuo to provide 2,6-dichloro-3-methoxypyridine (17.0 g, yield: 96.0%). 1H-NMR (CDCl3, 400 MHz) δ 7.12˜7.18 (m, 2H), 3.86 (s, 3H). MS (M+H)+: 178/180/182.

Workup

  1. extractionextracted with EtOAc (200 mL×3)
  2. washThe organic layer was washed with brine (200 mL×3)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-6b30bdf6aa0e40d780f29266bb682eb4
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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