2-Amino-5-bromo-4-methyl-3-nitropyridine → 5-Bromo-4-methylpyridine-2,3-diamine
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[C:5]([Br:12])=[CH:4][N:3]=1>Cl.[Fe]>[Br:12][C:5]1[C:6]([CH3:11])=[C:7]([NH2:8])[C:2]([NH2:1])=[N:3][CH:4]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Amino-5-bromo-4-methyl-3-nitropyridine (5 g) was dissolved in 6M HCl (50 mL) and iron powder was slowly added. The reaction was then heated to reflux until no starting material was seen via HPLC. The reaction was then cooled to room temperature and filtered. The bis-HCl salt was dried to a cream solid which was then taken up in EtOAc, neutralized with 50% NaOH solution to yield 5-bromo-4-methylpyridine-2,3-diamine as a free base.
Workup
- temperatureThe reaction was then heated
- temperatureto reflux until no starting material
- filtrationfiltered
- dry with materialThe bis-HCl salt was dried to a cream solid which
Sources & evidence
- ORD record
- ord-50a004bff53548748da3cb000baa2d26
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846664B2
Reaction notes
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