2-Amino-5-bromo-3-methylpyridine → HCID 178422464, compound

HRID 1816984Notes

Reaction equation

HRID 1816984 reaction equation
N[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.N([O-])=[O:11].[Na+]>OS(O)(=O)=O.O>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([OH:11])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 1379342-Amino-5-bromo-3-methylpyridineHCID 23668193Sodium Nitrite

Product 1

HCID 178422464HCID 178422464, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

2-Amino-5-bromo-3-methylpyridine (5.0 g, 26.7 mmol) in 2.6M H2SO4 (70 mL) was treated with sodium nitrite (5.0 g, 72.5 mmol) in water (10 mL) dropwise at 0° C. The mixture was allowed to warm to ambient temperature and stir for 1.5 hours. The mixture was filtered and the filtercake washed with cold water. The filtercake was dissolved in dichloromethane (100 mL), dried (MgSO4), and concentrated to provide the title compound (4.2 g, 84% yield). MS (DCI/NH3) m/z 188/190 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtercake washed with cold water
  3. dissolutionThe filtercake was dissolved in dichloromethane (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-23370b6e35014ffaab37a01b21137d5b
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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