Hydrochloric Acid → octyl nicotinate N-oxide

HRID 847351

Reaktionsgleichung

Reaktionsgleichung von HRID 847351
Cl.[CH2:2]([OH:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:11](O)(=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[N+:14]([O-:18])[CH:13]=1>>[C:11]([O:10][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[N+:14]([O-:18])[CH:13]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 9571-OctanolHCID 16976Oxiniacic Acid

Produkt 1

HCID 53734536octyl nicotinate N-oxideAusbeute 81,6 %

Versuchsvorschrift

Hydrogen chloride was bubbled through cold octanol (25 g, 190 mmol) until a weight gain of 4.2 g had registered. Nicotinic acid N-oxide (5.29 g, 38 mmol) was then added and the resulting mixture was stirred and heated at 95°-100° C. for 3 hours and 40 minutes. The excess octanol was then removed by distillation at reduced pressure, and the residue of the distillation was taken up in dichloromethane. The dichloromethane solution was washed with aqueous sodium bicarbonate and then with water, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was recrystallized from ligroine to give 7.73 g (31 mmol) of octyl nicotinate N-oxide, mp 69.5°-71° C.

Aufarbeitung

  1. temperatureheated at 95°-100° C. for 3 hours and 40 minutes
  2. customThe excess octanol was then removed by distillation at reduced pressure
  3. distillationthe residue of the distillation
  4. washThe dichloromethane solution was washed with aqueous sodium bicarbonate
  5. dry with materialwith water, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was recrystallized from ligroine

Quellen und Nachweise

ORD-Eintrag
ord-c757113ebaa94e8b8cd7bbc16f0d8f99
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05141839

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