Dimethylformamide → 5-Chloro-2-methoxy-4-methylpyridine

HRID 243770Notes

Reaction equation

HRID 243770 reaction equation
[Cl:1]N1C(=O)CCC1=O.CN(C)C=O.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][N:17]=1>O>[Cl:1][C:19]1[C:20]([CH3:22])=[CH:21][C:16]([O:15][CH3:14])=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 142234722-Methoxy-4-methylpyridine

Product 1

HCID 231336465-Chloro-2-methoxy-4-methylpyridineYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.2 g (69 mmol) of N-chlorosuccinimide was charged to a N,N-dimethylformamide (DMF) 15 ml solution of 8.0 g (65 mmol) of 2-methoxy-4-methylpyridine, followed by stirring for 18 hours. Water was added to the reaction solution, and the aqueous layer was extracted with diethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 8.5 g (yield: 82%) of 5-chloro-2-methoxy-4-methylpyridine (melting point 32 to 33° C.).

Workup

  1. extractionthe aqueous layer was extracted with diethyl ether
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationsubjected to filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4c353d4aa3f6416bbbface5d32c1028f
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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