Water → 2,6-Dibromopyridin-4-amine
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Br:11])[N:3]=1.O.[OH-].[Na+]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Br:11])[N:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 2,6-dibromo-4-nitro-pyridine (1.0 g, 3.54 mmol) in glacial acetic acid (20 mL) was added Fe-powder (1.0 g, 17.74 mmol) at room temperature. The reaction mixture was refluxed for 90° C. for 30 min. After completion of reaction (TLC monitoring), water was added (100 mL), basified with 2N NaOH (pH 12-14). The resulting mixture was filtered through celite-bed and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water, dried (Na2SO4), filtered and evaporated to dryness to get the desired product as an off white solid (0.80 g, 90%).
Workup
- additionwas added (100 mL)
- filtrationThe resulting mixture was filtered through celite-bed and
- extractionextracted with ethyl acetate (2×50 mL)
- washThe combined organic layers were washed with water
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1b684158232742d3bd98bb0143e665d6
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481544B2
Reaction notes
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