2-Amino-5-bromo-3-nitropyridine → 5-Bromopyridine-2,3-diamine

HRID 18215

Reaction equation

HRID 18215 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1>CCO>[Br:11][C:5]1[CH:6]=[C:7]([NH2:8])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

3

Reactant 1

HCID 1388782-Amino-5-bromo-3-nitropyridine

Product 1

HCID 6911565-Bromopyridine-2,3-diamineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-amino-5-bromo-3-nitropyridine (2.0 g, 9.17 mmole) in absolute EtOH (50 mL) was added SnCl2 hydrate (9.3 g, 41.3 mmole), then the mixture was heated to reflux. After 3 hr the mixture was cooled to RT and concentrated. The residue was taken up in 2.0 M NaOH and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the title compound (1.69 g, 98%) which was sufficiently pure for use in the next step: MS (ES) m/e 188/190 (M+H)+.

Workup

  1. temperaturethe mixture was heated to reflux
  2. concentrationconcentrated
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6d97c126179416eac70759d445f8bf5
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Linked notes

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