Carbon Dioxide → 2-Amino-5-bromo-3-hydroxypyridine

HRID 2266677Notes

Reaction equation

HRID 2266677 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[O:10]C(=O)[NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[Na+].C(=O)=O>>[NH2:8][C:5]1[C:4]([OH:10])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 136144586-Bromo-3H-oxazolo(4,5-b)pyridin-2-one

Product 1

HCID 116940412-Amino-5-bromo-3-hydroxypyridineYield 98%

Procedure

6-Bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in NaOH solution (2N, 250 mL, 500 mmol). The mixture was refluxed overnight and a clear solution was obtained. After cooling to room temperature, the reaction solution was neutralized to pH ˜7. A lot of CO2 was released and also precipitate was observed. The product was filtered, washed with water, and dried under high vacuum to provide 2-amino-5-bromo-pyridin-3-ol as an off-white solid (17.8 g, 98% yield).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customa clear solution was obtained
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-d15b9d1e545945d7b9aa313542f787cc
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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