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

HRID 243770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243770
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4c353d4aa3f6416bbbface5d32c1028f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653277B2

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