5-Fluoro-2-nitropyridin-3-ol → 2-Amino-5-fluoropyridin-3-ol

HRID 2275760Notes

Reaction equation

HRID 2275760 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-])=O)=[N:6][CH:7]=1>C(O)C.[Pd]>[NH2:8][C:5]1[C:4]([OH:11])=[CH:3][C:2]([F:1])=[CH:7][N:6]=1

Participants

4

Reactant 1

HCID 673878005-Fluoro-2-nitropyridin-3-ol

Product 1

HCID 214366912-Amino-5-fluoropyridin-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5.6 g of 5-fluoro-2-nitropyridin-3-ol (Example 7A; 36 mmol) were dissolved in 2 l of ethanol, a catalytic amount of palladium on activated carbon (10%) was added and the mixture was hydrogenated under standard hydrogen pressure for 16 h. The mixture was filtered off through silica gel and the filtrate was concentrated (product batch 1). The filter cake was rinsed with methanol until the colour of the filtrate was no longer yellowish. The filtrate was concentrated, giving a second product batch. This gave 4.26 g (85% of theory) of the title compound.

Workup

  1. customfor 16 h
  2. filtrationThe mixture was filtered off through silica gel
  3. concentrationthe filtrate was concentrated (product batch 1)
  4. washThe filter cake was rinsed with methanol until the colour of the filtrate
  5. concentrationThe filtrate was concentrated
  6. customgiving a second product batch

Sources & evidence

ORD record
ord-8bf4a03c44f64e78a33584384bf48b85
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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