Dimethylformamide → 2-Chloro-5-methoxypyridine

HRID 541148Notes

Reaction equation

HRID 541148 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-e3bd58d2ee4a48a0b11f5c784f2e9c5b
Source dataset
uspto-grants-2014_10
Patent number
US08871934B2

Reaction notes

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