Hydrochloric Acid → 5-Bromo-2-methoxypyridin-3-amine

Temperature

22.5 °C

Iron powder (1.17 kg) was added to a suspension of 5-bromo-2-(methyloxy)-3-nitropyridine (1.36 kg) in IMS (6.1 L), stirred under nitrogen at 20-25° C. Water (0.8 L) was then added and the mixture cooled to less than 10° C. Aqueous hydrochloric acid (0.8 L concentrated hydrochloric acid and 0.8 L water) was then added to the reaction mixture, maintaining the temperature below 10-15° C. The suspension was warmed to 20-25° C. and then stirred at this temperature for 23 hours. The suspension was filtered, the filter cake washed with IMS (2×2.7 L) and the combined filtrates concentrated under vacuum. Water (4.1 L) was added slowly to the concentrated solution and the resulting suspension was held at 20-25° C. for 1.75 hours. The resultant suspension was filtered, washed with water (2×6.8 L) and the solid dried under vacuum to give the title compound as an off-white solid (1.13 kg).

1. temperaturethe mixture cooled to less than 10° C
2. temperaturemaintaining the temperature below 10-15° C
3. temperatureThe suspension was warmed to 20-25° C.
4. stirringstirred at this temperature for 23 hours
5. filtrationThe suspension was filtered
6. washthe filter cake washed with IMS (2×2.7 L)
7. concentrationthe combined filtrates concentrated under vacuum
8. additionWater (4.1 L) was added slowly to the concentrated solution
9. filtrationThe resultant suspension was filtered
10. washwashed with water (2×6.8 L)
11. customthe solid dried under vacuum

ORD record

ord-3bd6b642172a45998b90e41cb3beb3a6

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09326987B2