Isopropanol → 4-Methyl-3-phenoxypyridine-1-oxide

HRID 851691Notes

Reaction equation

HRID 851691 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OO)(=[O:17])C.C(O)(C)C>C(O)(=O)C.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:17])=[CH:4][C:3]=1[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 6585Peracetic Acid2×HCID 30169024-Methyl-3-phenoxypyridine

Product 1

HCID 131457884-Methyl-3-phenoxypyridine-1-oxide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 25 g of 4-methyl-3-phenoxypyridine, [J.Med.Chem., 18, 1 (1975)] in 90 ml of glacial acetic acid is treated with 30 ml of 40% peracetic acid in acetic acid and the mixture is stirred and heated at 60° C. for 12 hours. Two further 10 ml portions of 40% peracetic acid are added and the mixture heated 4 hours at 60° C. 100 ml of isopropanol is added and the mixture is heated at 90° C. for 4 hours. The mixture is stripped at reduced pressure and dissolved in 500 ml of dichloromethane. The organic layer is washed with an excess of 25% sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered, concentrated, and distilled to yield 4-methyl-3-phenoxypyridine-1-oxide. B.P. 150°-152° C./0.3 mm

Workup

  1. temperaturethe mixture heated 4 hours at 60° C
  2. temperaturethe mixture is heated at 90° C. for 4 hours
  3. washThe organic layer is washed with an excess of 25% sodium hydroxide solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-59dcd2b3666749b7a05e9b8b1db69bd6
Source dataset
uspto-grants-1983_05
Patent number
US04386094

Reaction notes

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