3-(2-Fluoro-5-nitrophenyl)pyridine → 4-Fluoro-3-(pyridin-3-yl)aniline

HRID 1180219Notes

Reaction equation

HRID 1180219 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[H][H]>CCO.CCOC(C)=O.O=[Pt]=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 179648273-(2-Fluoro-5-nitrophenyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 222853304-Fluoro-3-(pyridin-3-yl)anilineYield 100%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-(2-fluoro-5-nitrophenyl)pyridine (26 g, 119 mmol) in EtOH (200 ml) and EtOAc (200 ml) was treated with PtO2 (1.35 g, 6 mmol) then exposed to 50 psi hydrogen until uptake ceased (circa 3 hours). The reaction was filtered through glass-microfibre filter paper and concentrated to gave 3-(2-fluoro-5-aminophenyl)pyridine (22.4 g) as a dark oil which solidified on standing: δH (360 MHz, CDCl3) 3.65 (2H, s), 6.65-6.72 (2H, m), 6.99 (1H, dd, J 9 and 9), 7.33-7.37 (1H, m), 7.84-7.86 (1H, m), 8.58 (1H, d, J 4), 8.76 (1H, m).

Workup

  1. custom(circa 3 hours)
  2. filtrationThe reaction was filtered through glass-microfibre filter paper
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-82b3ac4512564fbe93ec612b880b3a5a
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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