Hydrogen Peroxide → 5-Fluoro-3-pyridinol N-oxide

HRID 2377581Notes

Reaction equation

HRID 2377581 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[OH:9]O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N+:6]([O-:9])[CH:7]=1

Participants

4

Conditions

Temperature
70 °C

Procedure

A solution of 1.5 g (13.26 mmol) of 5-fluoro-3-pyridinol in 8 ml of acetic acid is heated to 70° C. and 1.25 ml (14.6 mmol) of 35% hydrogen peroxide are added gradually. The reaction mixture is stirred for 15 hours at 70° C. and then concentrated under reduced pressure; 50 ml of cold water are added to the evaporation residue and the mixture is stirred for 1 hour. The precipitate obtained is filtered off, rinsed with water and with a minimum amount of cold ethyl acetate on the filter and then dried to give 930 mg of the expected product in the form of a white powder (yield=55%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. addition50 ml of cold water are added to the evaporation residue
  3. stirringthe mixture is stirred for 1 hour
  4. customThe precipitate obtained
  5. filtrationis filtered off
  6. washrinsed with water and with a minimum amount of cold ethyl acetate on the
  7. filtrationfilter
  8. customdried

Sources & evidence

ORD record
ord-ee6bc25e092a404381519232f7ccdcc1
Source dataset
uspto-grants-2008_12
Patent number
US07470671B2

Reaction notes

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