2-Amino-5-bromopyridine → HCID 178526354, compound

Temperature

50 °C

To a 1 L round-bottom flask was added 2-amino-5-bromopyridine (100 g, 578 mmol), DMF-DMA (101 mL, 751 mmol) and 2-propanol (200 mL). The mixture was heated to reflux for 3H to give a clear dark solution. It was then cooled to 50° C. and hydroxylamine hydrochloride (52.2 g, 751 mmol) was added. The mixture was stirred at 50° C. overnight to give a yellow suspension. The precipitate was collected by filtration. The black filtrate was concentrated and the residue was stirred in EtOH (20 mL) for 20 min. The solid was collected by filtration. The combined solids were dried in an oven to give N-(5-bromopyridin-2-yl)-N′-hydroxyformimidamide as a sandy solid (94 g, 75% yield).

1. temperatureThe mixture was heated
2. temperatureto reflux for 3H
3. customto give a clear dark solution
4. customto give a yellow suspension
5. filtrationThe precipitate was collected by filtration
6. concentrationThe black filtrate was concentrated
7. stirringthe residue was stirred in EtOH (20 mL) for 20 min
8. filtrationThe solid was collected by filtration
9. customThe combined solids were dried in an oven

ORD record

ord-09e73350d3e54e55bbb78e56dc4df27c

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815894B2