Acetic Anhydride → 3-octyl-6-(4-octyloxyphenyl)-1H-2-pyridone

HRID 1780543Notes

Reaction equation

HRID 1780543 reaction equation
[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][CH:17]=2)=[N+:13]([O-])[CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(OC(=O)C)(=[O:33])C>>[CH2:1]([C:9]1[C:14](=[O:33])[NH:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 543682835-octyl-2-(4-octyloxyphenyl)pyridine N-oxide

Product 1

HCID 190469563-octyl-6-(4-octyloxyphenyl)-1H-2-pyridone

Procedure

2.20 g (5.4 mmol) of 5-octyl-2-(4-octyloxyphenyl)pyridine N-oxide are refluxed in 30 ml of acetic anhydride for 4 hours. The acetic anhydride is then distilled off, and the residue is taken up in 10 ml of 1:1 methylene chloride/methanol, and the mixture is stirred with methanolic potassium hydroxide solution for 1 hour. Washing with water and concentrated ammonium chloride solution, drying over sodium sulfate, filtration, removal of the solvent by distillation and recrystallization from 8:2 n-hexane/ethyl acetate give 1.79 g of 3-octyl-6-(4-octyloxyphenyl)-1H-2-pyridone. ##STR14##

Workup

  1. distillationThe acetic anhydride is then distilled off
  2. washWashing with water and concentrated ammonium chloride solution
  3. dry with materialdrying over sodium sulfate, filtration, removal of the solvent by distillation and recrystallization from 8:2 n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-9356afaf2f2f43f28739f6c2a4db3e1d
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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