Bromine → 2-Amino-5-bromo-3-(hydroxymethyl)pyridine

HRID 82904Notes

Reaction equation

HRID 82904 reaction equation
[Br:1]Br.[NH2:3][C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][N:5]=1>C(O)(=O)C>[NH2:3][C:4]1[C:9]([CH2:10][OH:11])=[CH:8][C:7]([Br:1])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 11159325(2-Aminopyridin-3-yl)methanol

Product 1

HCID 108913662-Amino-5-bromo-3-(hydroxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (10.4 mL, 202 mmol) was added dropwise over 1 hour to a solution of 2-amino-3-(hydroxymethyl)pyridine (25.1 g, 202 mmol) in acetic acid (500 mL) at room temperature. After complete addition the reaction mixture was stirred for an extra hour. After concentration to dryness, the residue was partitioned between 1M Na2CO3 (750 mL) and ethyl acetate (500 mL). The aqueous layer was separated and extracted one more time with ethyl acetate (500 mL). The combined organic phases were washed with a saturated solution of sodium chloride (500 mL), dried over sodium sulfate, filtered and concentrated to dryness. After trituration of the residue in DCM/heptane and extra washing with DCM the title product was obtained as a light yellow solid (30.0 g, 70%, py 97.3%).

Workup

  1. additionAfter complete addition the reaction mixture
  2. concentrationAfter concentration to dryness
  3. customthe residue was partitioned between 1M Na2CO3 (750 mL) and ethyl acetate (500 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted one more time with ethyl acetate (500 mL)
  6. washThe combined organic phases were washed with a saturated solution of sodium chloride (500 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. washAfter trituration of the residue in DCM/heptane and extra washing with DCM the title product
  11. customwas obtained as a light yellow solid (30.0 g, 70%, py 97.3%)

Sources & evidence

ORD record
ord-3a86a9eaded740f2b1c5892377322a6d
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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