HCID 22285303, compound → 4-Fluoro-3-(pyridin-4-yl)aniline

HRID 2183937Notes

Reaction equation

HRID 2183937 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:16]=[CH:15][N:14]=[CH:13][CH:12]=1>C(O)C.C(OCC)(=O)C.[Pt](=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 22285303HCID 22285303, compound

Product 1

HCID 222852664-Fluoro-3-(pyridin-4-yl)anilineYield 100%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-fluoro-5-nitrophenyl)pyridine (1.0 g, 5.58 mmol) in ethanol (30 ml) and ethyl acetate (10 ml) was added platinum(IV) oxide (52 mg) and the mixture stirred for 35 min under hydrogen (40 psi). The reaction was filtered through glass microfibre filter paper and the filtrate evaporated to dryness to give 4-fluoro-3-(pyridin-4-yl)phenylamine (862 mg, 100%) as a white solid: δH (360 MHz, CDCl3) 3.49 (2H, s), 6.66-6.70 (1H, m), 6.71-6.76 (1H, m), 6.99 (1H, t, J 9), 7.44-7.46 (2H, m), 8.66 (2H, d, J 5).

Workup

  1. filtrationThe reaction was filtered through glass microfibre
  2. filtrationfilter paper
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-bf47f441a2444eb3b12f5c230cb449c7
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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