Hydrochloric Acid → 2-Chloro-3-hydroxy-6-iodopyridine

After dissolving 2-chloro-3-hydroxypyridine (5.00 g, 38.6 mmol) and sodium iodide (5.79 g, 38.6 mmol) in dimethylformamide (70 ml), Chloramine T (10.9 g, 38.6 mmol) was added while cooling on ice, and then the mixture was stirred at room temperature for 1 hour. Upon adding 2N aqueous hydrochloric acid (19.3 ml, 38.6 mmol) after the reaction, the reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:hexane=1:2), and the fraction containing the target substance was concentrated to obtain the title compound (9.00 g, 35.2 mmol, 91%) as colorless crystals.

1. additionwas added
2. temperaturewhile cooling on ice
3. customafter the reaction
4. washthe organic layer was washed with water and saturated saline
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationthe drying agent was filtered off
7. distillationthe filtrate was distilled off under reduced pressure
8. customThe obtained crude product
9. additionthe fraction containing the target substance
10. concentrationwas concentrated

ORD record

ord-8aaf834e55664c51bfd51805daae7681

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372981B2