Methyl iodide → 2,5-Dichloro-4-methoxypyridine

HRID 1908813Notes

Reaction equation

HRID 1908813 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([Cl:9])=[CH:4][N:3]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CC(=O)OCC>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:10])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178516192HCID 178516192, compound

Product 1

HCID 714638062,5-Dichloro-4-methoxypyridineYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,5-dichloro-4-hydroxypyridine (1.43 g, 8.73 mmol) in DMF (15 mL), K2CO3 (2.41 g, 17.5 mmol) followed by methyl iodide (1.48 g, 8.73 mmol) is added. The mixture is stirred at rt for 24 h before it is diluted with EA (200 mL), washed with water (2×100 mL), dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 1:1 to give 2,5-dichloro-4-methoxy-pyridine (0.73 g) as a white solid; LC-MS: tR=0.85 min; [M+1]+=177.90.

Workup

  1. additionis added
  2. washwashed with water (2×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 1:1

Sources & evidence

ORD record
ord-344f1705119e43c1814c8609c679a8d6
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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