Bromine → 5-Bromo-4-propylpyridine-2-amine

HRID 1038546Notes

Reaction equation

HRID 1038546 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH2:10])[CH:5]=1)[CH2:2][CH3:3].[Br:11]Br.C(=O)([O-])O.[Na+]>C(O)C>[Br:11][C:9]1[C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][C:6]([NH2:10])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 70225944-Propylpyridin-2-amine

Product 1

HCID 665984465-Bromo-4-propylpyridine-2-amineYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4-propylpyridin-2-amine (5.70 g, 41.8 mmol) in ethanol (210 mL), a solution of bromine in ethanol (bromine 2.38 mL/ethanol 50 mL) was added under ice-cold conditions, and the mixture was stirred under ice-cold conditions for 0.5 hours. Under ice-cold conditions, the reaction solution was added an aqueous solution of sodium hydrogen carbonate, concentrated in vacuo, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (4.34 g (yield 48%)) was obtained as a brown oil.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4b474b17b47a42eb9175d6def1badd3e
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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