Hydrochloric Acid → octyl nicotinate N-oxide

HRID 847353Notes

Reaction equation

HRID 847353 reaction equation
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

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9571-OctanolHCID 16976Oxiniacic Acid

Product 1

HCID 53734536octyl nicotinate N-oxideYield 81.6%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-39a1b65bef2c44058762493d9af7f57e
Source dataset
uspto-grants-1992_08
Patent number
US05141842

Reaction notes

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