Dimethylformamide → 2-Chloro-5-methoxypyridine

HRID 1799029Notes

Reaction equation

HRID 1799029 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11](O)=[CH:10][N:9]=1.CI.CN(C)C=O>C(OCC)(=O)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([O:4][CH3:1])=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 151690002-Chloro-5-methoxypyridineYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, potassium carbonate (5.52 g) was added to a mixture of 2-chloro-5-hydroxy-pyridine (2.591 g), methyl iodide (1.50 ml) and dimethylformamide (26 ml), and the mixture was stirred at room temperature for 18 hr. To the reaction mixture was added ethyl acetate and the mixture was placed in a separatory funnel. The organic layer was washed 4 times with aqueous ammonium chloride, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (2.403 g, 84%).

Workup

  1. customthe mixture was placed in a separatory funnel
  2. washThe organic layer was washed 4 times with aqueous ammonium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e51f72287a884cefa05e28294f841c59
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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