反应详情

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+).

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