4-Fluoro-3-nitrophenol → 3-Amino-4-fluorophenol

HRID 1976937Notes

Reaction equation

HRID 1976937 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-])=O>[Pd].C(OCC)(=O)C>[NH2:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 167518614-Fluoro-3-nitrophenol

Product 1

HCID 135191803-Amino-4-fluorophenolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-fluoro-3-nitrophenol (2.70 g, 17.2 mmol) and palladium on charcoal (10%, 0.31 g) in 60 mL ethyl acetate is hydrogenated under 50 psi of H2 using a Parr hydrogenation reactor. After shaking for 1 hour, the reaction mixture is filtered using a diatomaceous earth pad to remove catalyst. The filtrate is concentrated in vacuo, and the residue is sublimed to yield 2.18 g (100%) of Compound 24 as a white solid. MP: 142-144° C. 1H-NMR (d6-DMSO) 8.82 (s, 1H); 6.70 (dd, 1H); 6.17 (dd, 1H); 5.85 (m, 1H); 4.92 (s, 2H). 19F-NMR (d6-DMSO) 142.78 (t, J=13.0 Hz). Anal. calc. for C6H6FNO: C, 56.69; H, 4.76; N, 11.02. Found: C, 57.28; H, 4.86; N, 10.65.

Workup

  1. filtrationthe reaction mixture is filtered
  2. customto remove catalyst
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-652852ad0c734fec9ecc6d41e7a297e8
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

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