1-Butanol → 2-Hydrazinyl-3-methoxypyridine

HRID 564862

Reaktionsgleichung

Reaktionsgleichung von HRID 564862
C(O)CCC.Cl[C:7]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][N:8]=1.O.[NH2:16][NH2:17].C(=O)([O-])[O-].[K+].[K+]>O>[NH:16]([C:7]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][N:8]=1)[NH2:17]

Komponenten

6

Edukt 4

HCID 2631-ButanolHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 1042522-Chloro-3-methoxypyridine

Produkt 1

HCID 185454042-Hydrazinyl-3-methoxypyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 50 ml of a butanol solution of 9.376 g of 2-chloro-3-methoxypyridine were added 16 ml of hydrazine monohydrate and 9.03 g of anhydrous potassium carbonate, and the mixture was heated under reflux for 20 hours. After cooling, the reaction mixture was poured into 200 ml of water and extracted with a mixed solvent of methanol-chloroform (1:9 by volume). The organic layer was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation. The residue was subjected to silica gel column chromatography using a mixture of chloroform-methanol (20:1 by volume) as an eluate. The fraction containing the desired compound was concentrated to afford 5.952 g of the title compound.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. temperatureAfter cooling
  4. extractionextracted with a mixed solvent of methanol-chloroform (1:9 by volume)
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation
  8. additiona mixture of chloroform-methanol (20:1 by volume) as an eluate
  9. additionThe fraction containing the desired compound
  10. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2904f9b1bac34986b09014d2022e536f
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169086A

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