Sodium Hydroxide → 2-Pyridinamine, 5-bromo-6-methyl-

HRID 1457771Notes

Reaction equation

HRID 1457771 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[Br:9]Br.[OH-].[Na+]>S(=O)(=O)(O)O.O>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 157652-Amino-6-methylpyridineHCID 24408Bromine

Product 1

HCID 1706782-Pyridinamine, 5-bromo-6-methyl-Yield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

32.4 g(0.3 mole) of 6-aminopicoline was dissolved in a mixture of 28 g of conc. sulfuric acid and 120 ml of water and the resulting solution was cooled in ice water. 52.8 g(0.33 mole) of bromine was added dropwise to the solution over 30 minutes at 0° C. The reaction solution was stirred for 20 minutes at room temperature and neutralized with cold aqueous NaOH solution. The resultant was filtered and purified by column chromatography using methylene chloride and ethyl acetate as an eluent to obtain 31 g of the title compound(yield 55%).

Workup

  1. filtrationThe resultant was filtered
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-0374f941d5c447fdb6df50c065d5b278
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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