Trifluoroacetic anhydride → 2-Propoxy-5-iodonicotinic acid

HRID 1636005Notes

Reaction equation

HRID 1636005 reaction equation
[I:1]NC(=O)CCC(N)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:23]([O:26][C:27]1[N:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([OH:31])=[O:30])[CH2:24][CH3:25]>FC(F)(F)C(O)=O>[CH2:23]([O:26][C:27]1[N:35]=[CH:34][C:33]([I:1])=[CH:32][C:28]=1[C:29]([OH:31])=[O:30])[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 21864724N-IodosuccinamideHCID 22648221HCID 22648221, compound

Product 1

HCID 116380942-Propoxy-5-iodonicotinic 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-propoxynicotinic acid (0.054 mol). The mixture was refluxed for 2.5h, 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 solid; 1H NMR (300 MHz, CDCl3): δ=1.05 (t, 3H), 1.85-2.0 (m, 2H), 4.5 (t, 2H), 8.5 (s, 1H), 8.6 (s, 1H), Analysis: found C, 35.16; H, 3.19; N, 4.46. Calcd for C9H10INO3: C, 35.19; H, 3.28; N, 4.56%; LRMS (TSP): 529.5 (MH+).

Workup

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

Sources & evidence

ORD record
ord-ba038c7575684903abe6852b473072f4
Source dataset
uspto-grants-2003_01
Patent number
US06512002B2

Reaction notes

Loading…