N-bromobutanimide → 5-Bromo-6-chloropyridin-2-amine

HRID 2382770Notes

Reaction equation

HRID 2382770 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[N:11]=1>CN(C=O)C>[Br:1][C:13]1[CH:14]=[CH:15][C:10]([NH2:9])=[N:11][C:12]=1[Cl:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 223492035-Bromo-6-chloropyridin-2-amineYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-bromosuccinimide (16.45 g; 92.41 mmol; 1.10 eq.) was added portionwise to a solution of 2-amino-6-chloropyridine (10.80 g; 84.01 mmol; 1.0 eq.) in DMF (200 mL) at rt. The reaction mixture was stirred at rt for 2 hours. Solvents were removed under reduced pressure and the residue was taken up in EtOAc and aqueous ammonia. The organic phase was washed again with aqueous ammonia and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The black solid obtained was washed with pentane and dried under vacuum to give the title compound as a beige powder (12.5 g, 72%). HPLC, Rt: 2.81 min. (purity 95.8%).

Workup

  1. customSolvents were removed under reduced pressure
  2. washThe organic phase was washed again with aqueous ammonia and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe black solid obtained
  7. washwas washed with pentane
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8ce3d7d7a92a44568a90e7b34a785037
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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