Sodium Hydroxide → 3-Amino-5-bromo-2-chloropyridine

A suspension of 5-bromo-2-chloro-3-nitropyridine (Combi-Blocks, San Diego, USA, 41.3 mmol) in concentrated HCl (45 ml) was cooled with an ice-bath. Was added portionwise over 1.5 h SnCl2 dihydrate (124 mmol). The RM was stirred for 24 h at rt then poured on ice and basified with 6 M aqueous NaOH (125 ml). The resulting slurry was filtered and the solid was taken in aqueous NaHCO3, sonicated and filtered. The solid was dissolved in EtOAc and water and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4, filtered and evaporated to give the title compound as an off-white solid. (HPLC: tR 2.52 min (Method A); M+H=207 (BrCl pattern) MS-ES)

1. temperaturewas cooled with an ice-bath
2. additionthen poured on ice
3. filtrationThe resulting slurry was filtered
4. customsonicated
5. filtrationfiltered
6. dissolutionThe solid was dissolved in EtOAc
7. customwater and the aqueous layer was separated
8. extractionextracted with EtOAc
9. washThe combined organic layers were washed with water, brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. customevaporated

ORD record

ord-44e307e5798f450c9e1971b842074c91

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2