Sulfuric Acid → HCID 178422464, compound

HRID 2307863Notes

Reaction equation

HRID 2307863 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:11]([CH3:12])=[CH:10][C:9]([Br:13])=[CH:8][N:7]=1.S(=O)(=O)(O)[OH:15]>O>[Br:13][C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([OH:15])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1379342-Amino-5-bromo-3-methylpyridineHCID 23668193Sodium Nitrite

Product 1

HCID 178422464HCID 178422464, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-0dd694d4e4f645aabe94b8f042dedf8c
Source dataset
uspto-grants-2004_12
Patent number
US06833370B1

Reaction notes

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