Sodium Azide → 3-Azidoacetylpyridine

HRID 1639706Notes

Reaction equation

HRID 1639706 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[N-:12]=[N+:13]=[N-:14].[Na+].C([O-])(O)=O.[Na+]>O>[N:12]([CH2:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Product 1

HCID 593028753-Azidoacetylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-bromoacetylpyridine hydrobromide (5 g, 17.8 mmol) in 20 mL of water was added sodium azide (1.16 g, 17.8 mmol) and the contents stirred at room temperature for 2 h. The reaction mixture was treated with saturated aqueous NaHCO3 until neutrality, extracted with ethyl acetate (3×30 mL) and the combined organic phases were dried over MgSO4. After solvent removal the crude residue was silica gel column chromatographed (dichloromethane/ethanol/98/2). 3-Azidoacetyl-pyridine was obtained as yellow solid (2.17 g, 71%).

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. dry with materialthe combined organic phases were dried over MgSO4
  3. customAfter solvent removal the crude residue
  4. customchromatographed (dichloromethane/ethanol/98/2)

Sources & evidence

ORD record
ord-4aa43ef56d3548d4bdd4a50c889542ad
Source dataset
uspto-grants-2012_02
Patent number
US08110591B2

Reaction notes

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