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

HRID 2264177

Reaktionsgleichung

Reaktionsgleichung von HRID 2264177
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 595960023-Bromo-5-nitro-2,3'-bipyridin-6-amineAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-599d982637a347b980b45430f25fa1f0
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855202B2

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