5-Fluoro-3-nitropyridin-2-amine → 5-Fluoro-2,3-pyridinediamine

HRID 656946Notes

Reaction equation

HRID 656946 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 217173395-Fluoro-3-nitropyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 222931555-Fluoro-2,3-pyridinediamineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5-fluoro-3-nitro-2-pyridinamine (561 mg, 3.573 mmol) in ethanol (100 ml) was treated with added 10% Pd/C (100 mg) and the mixture was then stirred at rt under 1 atmosphere of hydrogen for 5 h. The reaction mixture was then filtered through a thin pad of Celite, washing through with EtOH (500 ml). The filtrate was evaporated to give the desired product as a grey solid (435 mg, 96%).

Workup

  1. additionwas treated
  2. filtrationThe reaction mixture was then filtered through a thin pad of Celite
  3. washwashing through with EtOH (500 ml)
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-1019a05630c247999b970446eef3d820
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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