5-Bromo-4,6-dimethylpyridin-2-amine → HCID 178429301, compound

HRID 1043890Notes

Reaction equation

HRID 1043890 reaction equation
N[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1.N([O-])=[O:12].[Na+]>S(=O)(=O)(O)O.O>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([OH:12])=[N:3][C:4]=1[CH3:10]

Participants

5

Reactant 2

HCID 110308555-Bromo-4,6-dimethylpyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 178429301HCID 178429301, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

2-amino-5-bromo-4,6-dimethylpyridine (15 g) was dissolved in a mixed solution of sulfuric acid (14.2 mL) and water (212 mL). A solution of sodium nitrite (6.18 g) in water (31 mL) was added to the solution at 0° C. The reaction mixture was stirred at mom temperature for one hour, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the desiccant was filtered off. The filtrate was concentrated under reduced pressure. MTBE was added to the residue to precipitate the solid, followed by filtration. The filtration residue was washed with MTBE to give the title compound (13.7 g).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionMTBE was added to the residue
  6. customto precipitate the solid
  7. filtrationfollowed by filtration
  8. washThe filtration residue was washed with MTBE

Sources & evidence

ORD record
ord-a776de9b47cf4981b1071060197f4f51
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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