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

HRID 1844124Notes

Reaction equation

HRID 1844124 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 10A; 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 hydrogen standard pressure for 16 h. The mixture was filtered off through kieselguhr and the filtrate was concentrated (product batch 1). The residue 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 a total of 4.26 g (85% of theory) of the title compound.

Workup

  1. customfor 16 h
  2. filtrationThe mixture was filtered off through kieselguhr
  3. concentrationthe filtrate was concentrated (product batch 1)
  4. washThe residue 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-ea201032b38a443398609559a6258995
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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