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

HRID 2055432Notes

Reaction equation

HRID 2055432 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[C:11]([CH3:12])=[CH:10][C:9]([Br:13])=[CH:8][N:7]=1>O.S(=O)(=O)(O)O>[Br:13][C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([OH:2])=[N:7][CH:8]=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

Sodium nitrite (5.0 g, 72.5 mmol) in water (10 mL) was added dropwise to a cooled (0° C.) mixture of 2-amino-5-bromo-3-methylpyridine (5.0 g, 26.7 mmol; Lancaster) in 2.6 M sulfuric acid (70 mL). The mixture was allowed to warm to ambient temperature, stir for 1.5 hours, filtered, and the filtercake was washed with cold water and air dried. The precipitate was dissolved in dichloromethane (100 mL), dried (MgSO4), and concentrated to provide the title compound as a solid (4.2 g, 84%). MS (DCI/NH3) m/z 348 (M+H)+.

Workup

  1. temperaturea cooled
  2. filtrationfiltered
  3. washthe filtercake was washed with cold water and air
  4. customdried
  5. dissolutionThe precipitate was dissolved in dichloromethane (100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-35e8a113e4034b2394a46ddbd6bfc1f8
Source dataset
uspto-grants-2008_02
Patent number
US07332504B2

Reaction notes

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