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 3 h 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 3 h
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-4ffcf579a64b4b4e901793bd3b2bc699

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09173879B2