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

HRID 2176548Notes

Reaction equation

HRID 2176548 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.[Br:9]N1C(=O)CCC1=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 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 N-bromosuccinimide (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-81407d85ed3649d58ae0db157991f62d
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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