N-bromobutanimide → 3-Bromo-5-nitro-2,3'-bipyridin-6-amine

HRID 2264177Notes

Reaction equation

HRID 2264177 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:9]=1[NH2:10])([O-:3])=[O:2].[Br:17]N1C(=O)CCC1=O>CN(C=O)C>[Br:17][C:6]1[C:7]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:9]([NH2:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 205503675-Nitro-2,3'-bipyridin-6-amine

Product 1

HCID 595960023-Bromo-5-nitro-2,3'-bipyridin-6-amineYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. cooled stirred solution of 5-nitro-2,3′-bipyridin-6-amine (4.8 g, 22.2 mmol) in DMF (50 mL), N-bromosuccinimide (4.75 g, 26.7 mmol) was added in portions. After stirring at room temperature for 16 h, the solvent was removed under reduced pressure. The crude residue was solved with ethyl acetate and washed with saturated potassium carbonate aqueous solution. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel flash chromatography (95:5 dichloromethane/methanol) to give the title compound (6.6 g, 100%) as a solid.

Workup

  1. additionwas added in portions
  2. customthe solvent was removed under reduced pressure
  3. washwashed with saturated potassium carbonate aqueous solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by silica gel flash chromatography (95:5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-599d982637a347b980b45430f25fa1f0
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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