Isopropanol → HCID 54105304, compound

HRID 1448140Notes

Reaction equation

HRID 1448140 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.C(OO)(=[O:17])C.C(O)(C)C>C(O)(=O)C>[F:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N+:7]([O-:17])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6585Peracetic AcidHCID 12673483HCID 12673483, compound

Product 1

HCID 54105304HCID 54105304, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 30 g of 3-(o-fluorophenoxy)pyridine in 50 ml of glacial acetic acid is treated at 35° C. with 33 g of 40% peracetic acid in acetic acid in four portions. The mixture is stirred for 16 hours, refluxed 1 hour and 50 ml of isopropanol is added and the heating continued at 95° C. for 1 hour. The mixture is concentrated at reduced pressure and is dissolved in 300 ml of dichloromethane. The solution is washed with excess 25% sodium hydroxide solution. The dichloromethane solution is dryed over anhydrous MgSO4, filtered and concentrated at reduced pressure. The 3-(o-fluorophenoxy)-pyridine N-oxide crystallizes, mp 89°-95° C.

Workup

  1. temperaturerefluxed 1 hour
  2. waitthe heating continued at 95° C. for 1 hour
  3. concentrationThe mixture is concentrated at reduced pressure
  4. dissolutionis dissolved in 300 ml of dichloromethane
  5. washThe solution is washed with excess 25% sodium hydroxide solution
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customThe 3-(o-fluorophenoxy)-pyridine N-oxide crystallizes

Sources & evidence

ORD record
ord-24e54f018a224afdb3966ba6e9232599
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

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