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

HRID 1642156Notes

Reaction equation

HRID 1642156 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-2bfeafaf2cf0425dba34c800e7d996ef
Source dataset
uspto-grants-2012_02
Patent number
US08119635B2

Reaction notes

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