Sodium Azide → 3-Azidoacetylpyridine

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

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%).