N-bromobutanimide → 3-Bromo-2-chloropyridin-4-amine

HRID 503501Notes

Reaction equation

HRID 503501 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.C1C(=O)N([Br:16])C(=O)C1>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[C:3]=1[Br:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 844322-Chloropyridin-4-amine

Product 1

HCID 299193003-Bromo-2-chloropyridin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Amino-2-chloropyridine (50 g, 388 mmol) was dissolved in glacial acetic acid (500 mL). To this solution was added NBS (75 g, 426 mmol) portionwise at RT (water bath cooling was provided to control the exothermicity). The reaction mixture was stirred at RT for 1 h at which point the reaction was found complete (as monitored by TLC). Solvent was removed under reduced pressure followed by azeotropic distillation with ethanol. The crude product was purified by column chromatography on silica gel (230-400 mesh) eluting with ethyl acetate hexane mixture.

Workup

  1. temperaturecooling
  2. customwas provided
  3. customSolvent was removed under reduced pressure
  4. distillationfollowed by azeotropic distillation with ethanol
  5. customThe crude product was purified by column chromatography on silica gel (230-400 mesh)
  6. washeluting with ethyl acetate hexane mixture

Sources & evidence

ORD record
ord-6c3be5b444b84daba708f4d4a691daf9
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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