Bromine → HCID 178508959, compound

HRID 1848361Notes

Reaction equation

HRID 1848361 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[N:3]=1.[Br:9]Br>C(O)(=O)C>[NH2:1][C:2]1[N:3]=[C:4]([OH:8])[CH:5]=[CH:6][C:7]=1[Br:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 1785076342-Amino-6-hydroxypyridine

Product 1

HCID 178508959HCID 178508959, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under an argon atmosphere 2-amino-6-hydroxy-pyridine (19.6 g, 178 mmol) was suspended in acetic acid (100%, 390 mL). Br2 (9.2 mL, 178 mmol) was added at 20° C. over 5 min. The green suspension was stirred at RT for 20 min. The mixture was poured onto H2O (400 mL) and filtered. The filtrate was mixed with brine (200 mL) and extracted with EtOAc (10×400 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated to afford 6-Amino-5-bromo-pyridin-2-ol as a yellow solid (23 g).

Workup

  1. additionThe mixture was poured onto H2O (400 mL)
  2. filtrationfiltered
  3. additionThe filtrate was mixed with brine (200 mL)
  4. extractionextracted with EtOAc (10×400 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-67d97185f367497a8a7718dd8ad8a328
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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