Sulfuric Acid → 5-Bromo-4,6-dimethylpyridin-2-amine

HRID 1457788Notes

Reaction equation

HRID 1457788 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.S(=O)(=O)(O)O.[Br:15]Br.[OH-].[Na+]>O>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:15])=[C:4]([CH3:9])[N:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 215072-Amino-4,6-dimethylpyridineHCID 24408Bromine

Product 1

HCID 110308555-Bromo-4,6-dimethylpyridin-2-amineYield 55.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

20 g(0.164 mole) of 2-amino-4, 6-dimethylpyridine was added into a mixture of 69 ml of water and 16.1 g(0.164 mole) of sulfuric acid and the resulting solution was cooled to 0° C., and thereto was added 8.45 ml(0.164 mole) of bromine gradually at 0° C. The resulting solution was stirred for 30 minutes, adjusted to pH 9 to 10 with aqueous sodium hydroxide solution and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified with silica gel column chromatography to obtain 18.25 g of the title compound(yield 55%) and 5.4 g of dibromo compound(yield 11.8%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-195b49783a8848798ec22b76e2c4eef3
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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