Methyl iodide → 2-Chloro-5-methoxypyridine

HRID 1437257Notes

Reaction equation

HRID 1437257 reaction equation
[CH3:1][O-].[Na+].CO.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][N:8]=1.CI>CN(C)C=O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:1])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8198212-Chloro-5-hydroxypyridineHCID 23694274Sodium methanolate methanol

Product 1

HCID 151690002-Chloro-5-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28% Sodium methoxide-methanol (2.0 mL) was added dropwise to the above-obtained 2-chloro-5-hydroxypyridine (1.30 g) and methyl iodide (1.25 mL) in N,N-dimethylformamide (26 mL), followed by stirring at room temperature for 1.5 hours. The reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel chromatography (hexane-ethyl acetate), to thereby give 2-chloro-5-methoxypyridine as a solid (1.40 g, 98%).

Workup

  1. customThe reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydrate
  4. filtrationfollowed by filtration
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified through silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-96aa96b7f7df42afbb9ae6b0672b4dde
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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