N-Iodosuccinimide → 5-iodo-2-butoxynicotinic acid

N-Iodosuccinimide (6.0 g, 26.7 mmol) was added to a solution of 2-n-butoxypyridine-3-carboxylic acid (Preparation 4; 3.46 g, 17.7 mmol) in trifluoroacetic acid (28 mL) and trifluoroacetic anhydride (7 mL) and the reaction heated under reflux in the absence of light, for 3 hours. The cooled reaction mixture was concentrated under reduced pressure and the residue dissolved in ethyl acetate. This solution was washed sequentially with water (2×), aqueous sodium thiosulfate solution, aqueous sodium citrate solution, 2 N hydrochloric acid, and brine, then dried (MgSO4) and evaporated under reduced pressure. The solid was triturated with pentane, filtered, washed with additional pentane and dried, to give the title compound as a white solid (3.86 g, 68%).

1. temperaturethe reaction heated
2. temperatureunder reflux in the absence of light, for 3 hours
3. customThe cooled reaction mixture
4. concentrationwas concentrated under reduced pressure
5. dissolutionthe residue dissolved in ethyl acetate
6. washThis solution was washed sequentially with water (2×), aqueous sodium thiosulfate solution, aqueous sodium citrate solution, 2 N hydrochloric acid, and brine
7. dry with materialdried (MgSO4)
8. customevaporated under reduced pressure
9. customThe solid was triturated with pentane
10. filtrationfiltered
11. washwashed with additional pentane
12. customdried

ORD record

ord-15dc961f0c52456aa42fd5ae586693cd

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586439B2