2-Amino-5-bromo-4-methyl-3-nitropyridine → 5-bromo-4-methylpyridine-2,3-diamine

HRID 80556

Reaction equation

HRID 80556 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]=1

Participants

4

Reactant 1

HCID 72132072-Amino-5-bromo-4-methyl-3-nitropyridine

Product 1

HCID 101251415-bromo-4-methylpyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolvent

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

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until no starting material
  3. filtrationfiltered
  4. 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

Linked notes

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