Methanol → 2-Chloro-4-methoxy-5-methylpyridine

HRID 1908811Notes

Reaction equation

HRID 1908811 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[OH-:10].[Na+].[CH3:12]O>O>[Cl:1][C:2]1[CH:7]=[C:6]([O:10][CH3:12])[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 126437182,4-Dichloro-5-methylpyridine

Product 1

HCID 790022772-Chloro-4-methoxy-5-methylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2,4-dichloro-5-methyl-pyridine (337 mg, 2.08 mmol) in methanol (10 mL), NaOH (93 mg, 2.33 mmol) is added. The mixture is refluxed for 5 days before it is cooled to rt, diluted with water and extracted with EA. The org. extract is dried over MgSO4, filtered and concentrated to give 2-chloro-4-methoxy-5-methyl-pyridine (240 mg) as a white solid; 1H NMR (CDCl3): δ 2.15 (s, 3H), 3.90 (s, 3H), 6.77 (s, 1H), 8.02 (s, 1H); 13C NMR (CDCl): δ 12.67, 55.60, 105.77, 121.77, 149.50, 150.29, 165.41.

Workup

  1. temperatureThe mixture is refluxed for 5 days before it
  2. extractionextracted with EA
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-711d6c4847844443a4176d30cb8b6cc5
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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