Sodium Bicarbonate → 6-Chloro-4-iodopyridin-3-ol

Temperature

60 °C

2-Chloro-4-iodo-5-methoxymethoxy-pyridine (0.8 g, 2.7 mmol) was dissolved in THF (4 mL) and 3N HCl (6 mL). The mixture was heated to 60° C. with magnetic stirring. Heating was maintained for 3 hours. The mixture was cooled to room temperature and the pH was adjusted to 7 with the slow addition of saturated aqueous sodium bicarbonate. The result was extracted with EtOAc (3×50 mL) dried over Na2SO4, filtered and concentrated. The solid was suspended in EtOAc and stirred for 12 hours at room temperature. The mixture was filtered and the filtrate was concentrated to yield an off white solid (0.63 g, 93%). 1H NMR (400 MHz, DMSO-d6): δ11.10 (br s, 1H), 7.89 (s, 2H).

1. temperatureHeating
2. temperaturewas maintained for 3 hours
3. temperatureThe mixture was cooled to room temperature
4. extractionThe result was extracted with EtOAc (3×50 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. filtrationThe mixture was filtered
9. concentrationthe filtrate was concentrated

ORD record

ord-18e757f8e96e4342a72bb22914f75f0b

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2