Sodium Hydroxide → 5-Bromo-4,6-dimethylpyridin-2-amine

HRID 1455917Notes

Reaction equation

HRID 1455917 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Br:10]Br.[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:10])=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 110308555-Bromo-4,6-dimethylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

6.1 g (50 mmol) of 2-amino-4,6-dimethylpyridine are dissolved in 50 ml of acetic acid. A solution of 8 g (50 mmol) of bromine in 50 ml of acetic acid is added dropwise using a dropping funnel. The reaction medium is allowed to return to room temperature and the stirring is continued for 3 hours. The mixture is cooled in an ice bath and 40% sodium hydroxide is then added until the pH is basic. The mixture is filtered and dried. The residue is taken up in a little isopropyl ether and then chromatographed on silica gel, eluting with this same solvent. The expected product is collected in the form of white crystals. It is recrystallized from absolute ethanol.

Workup

  1. customto return to room temperature
  2. temperatureThe mixture is cooled in an ice bath
  3. filtrationThe mixture is filtered
  4. customdried
  5. customchromatographed on silica gel
  6. washeluting with this same solvent
  7. customThe expected product is collected in the form of white crystals
  8. customIt is recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-523e64c4527b4d1abd77788ce8460537
Source dataset
uspto-grants-1998_12
Patent number
US05843947

Reaction notes

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