2-Amino-5-bromo-3-methylpyridine → HCID 178422464, compound
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe mixture was filtered
- washthe filtercake washed with cold water
- dissolutionThe filtercake was dissolved in dichloromethane (100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b215675b2fac4e29878af11d8c1f0757
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809105B2
Reaction notes
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