Acetic Acid → HCID 69347098, compound

HRID 456999Notes

Reaction equation

HRID 456999 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2.N.C(O)(=[O:25])C>>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N+:10]2[O-:25]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 22139706HCID 22139706, compound

Product 1

HCID 69347098HCID 69347098, compoundYield 68%

Procedure

The solution of 5-(2,4-difluoro-phenoxy)-6-methoxy-quinoline in glacial acetic acid containing 4 ml hydrogen peroxide was stirred at 80–85° C. for 18 hours. After cooling the reaction mixture was neutralized with aqueous ammonia, and the resultant precipitate was filtered and washed with water. The aqueous layer was extracted with dichloromethane, and the organic layer was dried (MgSO4). Evaporation gave 1.3 g (68%) of 5-(2,4-difluoro-phenoxy)-6-methoxy-quinoline N-oxide as a beige crystalline material.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with water
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialthe organic layer was dried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-b89cedbe4b434a6a95e29fe168f21b68
Source dataset
uspto-grants-2007_03
Patent number
US07186840B2

Reaction notes

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