2-amino-5-bromopyridin-3-ol

Uses

2-Amino-5-bromo-3-hydroxypyridine is used as an organic chemical synthesis intermediate.

Synthesis

General procedure for the synthesis of 3-hydroxy-2-amino-5-bromopyridine from 6-bromo-3H-oxazolo[4,5-b]pyridin-2-one: 6-bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in 2N NaOH solution (250 mL, 500 mmol). The mixture was refluxed and reacted overnight until a clarified solution was formed. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently neutralized with acid to a pH of about 7. During this process, the release of large amounts of CO2 gas as well as the formation of a precipitate was observed. The precipitate was collected by filtration, washed with water and dried under high vacuum to give the final 2-amino-5-bromopyridin-3-ol as an off-white solid (17.8 g, 98% yield).

References

[1] Patent: US2006/46991, 2006, A1. Location in patent: Page/Page column 33-34
[2] Patent: WO2006/21886, 2006, A1. Location in patent: Page/Page column 64; 65
[3] Heterocycles, 2001, vol. 55, # 7, p. 1329 - 1345
[4] Heterocycles, 1995, vol. 41, # 12, p. 2799 - 2810
[5] Tetrahedron Letters, 2014, vol. 55, # 9, p. 1528 - 1531