Water → 4,5-Dichloro-2-methoxypyridine

HRID 1912250Notes

Reaction equation

HRID 1912250 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[Cl:10]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:1][C:2]1[C:7]([Cl:10])=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 226385104-Chloro-2-methoxypyridine

Product 1

HCID 230825824,5-Dichloro-2-methoxypyridineYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g (69.9 mmol) of crude 4-chloro-2-methoxypyridine obtained in Step (d) was dissolved in 100 ml of dimethylformamide, and 37.2 g (279 mmol) of N-chlorosuccinimide was added, followed by stirring at room temperature for 12 hours. 400 ml of water was added to terminate the reaction, followed by extraction with ethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 9.10 g (crude yield: 73%) of crude 4,5-dichloro-2-methoxypyridine.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionfollowed by extraction with ethyl ether
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationsubjected to filtration
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ce5b14f94aff44d6bc4afc82b5162880
Source dataset
uspto-grants-2013_12
Patent number
US08609150B2

Reaction notes

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