Trifluoroacetic anhydride → 5-Iodo-2-(2-methylpropoxy)-3-pyridinecarboxylic acid

HRID 354162Notes

Reaction equation

HRID 354162 reaction equation
[I:1]NC(=O)CCC(N)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:23]([O:27][C:28]1[N:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([OH:32])=[O:31])[CH:24]([CH3:26])[CH3:25]>FC(F)(F)C(O)=O>[CH2:23]([O:27][C:28]1[N:36]=[CH:35][C:34]([I:1])=[CH:33][C:29]=1[C:30]([OH:32])=[O:31])[CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 21864724N-IodosuccinamideHCID 235115682-(2-Methylpropoxy)pyridine-3-carboxylic acid

Product 1

HCID 235116705-Iodo-2-(2-methylpropoxy)-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-Iodosuccinamide (18.22 g, 0.08 mol), trifluoroacetic acid (100 mL) and trifluoroacetic anhydride (25 mL) were added to 2-isobutoxynicotinic acid (10.55 g, 0.054 mol). The mixture was refluxed for 2.5 h, cooled and the solvents evaporated. The residue was extracted from water with ethyl acetate and the organics washed with water (twice) and brine (twice), dried (MgSO4) and concentrated. The red residue was redissolved in ethyl acetate washed with sodium thiosulfate solution (twice), water (twice), brine (twice), redried (MgSO4) and concentrated to give the desired product as a yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 2.5 h
  2. temperaturecooled
  3. customthe solvents evaporated
  4. extractionThe residue was extracted from water with ethyl acetate
  5. washthe organics washed with water (twice) and brine (twice),
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe red residue was redissolved in ethyl acetate
  9. washwashed with sodium thiosulfate solution (twice), water (twice), brine (twice),
  10. dry with materialredried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-bba57e6b6047401db7b40bc061fbfbbd
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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