Sodium Carbonate → HCID 58765320, compound

HRID 860018Notes

Reaction equation

HRID 860018 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N+:10]([O-])=[CH:9][CH:8]=[CH:7]2.C(=O)([O-])[O-:18].[Na+].[Na+]>C(OC(=O)C)(=O)C>[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:18])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 22735319HCID 22735319, compound

Product 1

HCID 58765320HCID 58765320, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 6-trifluoromethoxy-quinoline 1-oxide of Step B (4.58 g, 20 mmol) in acetic anhydride (20 mL) is heated at 135° C. under nitrogen for 4 hours. The mixture is poured onto ice, carefully basified with sodium carbonate and extracted with ethyl acetate. The extracts are washed with brine, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is flash chromatographed on silica Merck-60 using a gradient of methanol (0–3%) in hexane-ethyl acetate (1:1). The appropriate fractions are combined and evaporated. The residue is triturated with diethyl ether. The insoluble is collected, washed with hexane and dried to provide the title compound as a pale brown crystalline solid (1.086 g), m.p. 215–217° C.

Workup

  1. additionThe mixture is poured onto ice
  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. customchromatographed on silica Merck-60
  7. customevaporated
  8. customThe residue is triturated with diethyl ether
  9. customThe insoluble is collected
  10. washwashed with hexane
  11. customdried

Sources & evidence

ORD record
ord-f0a4a0c6691648ed8ecd8419c4172393
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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