2-Chloropyridin-4-amine → 3-Bromo-2-chloropyridin-4-amine

HRID 219143

Reaction equation

HRID 219143 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.[Br:9]NC(=O)CCC(N)=O>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[C:3]=1[Br:9]

Participants

4

Reactant 2

HCID 844322-Chloropyridin-4-amineHCID 9834204N-Bromosuccinamide

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 N-bromosuccinamide (75 g, 426 mmol,) portionwise at room temperature (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-f49c884ff4b54645b8e49b4da4d9151a
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Linked notes

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