Hydrogen Peroxide → HCID 22735319, compound

HRID 860017Notes

Reaction equation

HRID 860017 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2.[OH:16]O.[OH-].[NH4+]>C(O)(=O)C>[F:15][C:2]([F:1])([F:14])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N+:10]([O-:16])=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 155503576-(Trifluoromethoxy)quinoline

Product 1

HCID 22735319HCID 22735319, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
82 °C

Procedure

To a solution of the crude 6-trifluoromethoxy-quinoline of Step A (obtained from 50 mmol of 4-trifluoromethoxy aniline) in glacial acetic acid (54 mL) is added dropwise 30% hydrogen peroxide (8 mL). The mixture is heated at 82° C. under nitrogen for 16 hours, cooled, carefully basified with concentrated ammonium hydroxide and extracted with ethyl acetate. The extracts are washed with brine, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is twice azeotroped with benzene, and then flash chromatographed on silica gel Merck-60 using dichloromethane followed by a gradient of methanol (0.5–2%) in dichloromethane to provide the title compound as a pale brown oil that solidifies upon standing. The pale brown crystals (4.8 g) melt at 68–70° C.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe extracts are washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue is twice azeotroped with benzene
  7. customflash chromatographed on silica gel

Sources & evidence

ORD record
ord-7f814ffc728446a69dfb0e6ee423ed46
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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