Water → 4,5-Dichloro-2-methoxypyridine

HRID 242409Notes

Reaction equation

HRID 242409 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-9a0b3b406c134a5eb2487a52be6dc8d3
Source dataset
uspto-grants-2014_02
Patent number
US08653113B2

Reaction notes

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