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

HRID 586259Notes

Reaction equation

HRID 586259 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: 1H NMR (360 MHz, CDCl3) δ 3.49 (2H, s), 6.66-6.70 (1H, m), 6.71-6.76 (1H, m), 6.99 (1H, t, J 9 Hz), 7.44-7.46 (2H, m), 8.66 (2H, d, J 5 Hz).

Workup

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

Sources & evidence

ORD record
ord-c532404391cc45b486de4aee34fdff6b
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

Loading…