Water → 4,5-Dichloro-2-methoxypyridine

HRID 243759Notes

Reaction equation

HRID 243759 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-b8e7891fd4b34f93a511a052302fc01c
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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