Methane → 4-(Pyridin-4-yl)aniline

HRID 2236493Notes

Reaction equation

HRID 2236493 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.C.O.NN>CO>[N:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 2592194-(4-Nitrophenyl)pyridine

Product 1

HCID 15126544-(Pyridin-4-yl)anilineYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-nitro-phenyl)-pyridine (250 mg, 1.25 mmol) is dissolved in MeOH (20 mL). To this solution is added FeCl3.6H2O (24 mg, 0.09 mmol) and active charcoal (12 mg, 1.0 mmol). The suspension is heated to reflux. Hydrazine hydrate (1.3 mL) is added, and reflux is continued for 3 h. After the mixture is cooled to room temperature, the active charcoal is filtered off through Celite, and the MeOH is removed under reduced pressure. The residue is purified with flash chromatography to provide the 4-pyridin-4-yl-phenylamine (200 mg, 94%). 1H NMR (400 MHz, CDCl3) ∂ 8.57 (2H, d, J=8.8 Hz), 7.44-7.52 (4H, m), 6.77 (2H, d, J=7.2 Hz), 3.87 (2H, br); MS (ESI) m/z 171 (M+H)+1.

Workup

  1. temperatureThe suspension is heated to reflux
  2. temperaturereflux
  3. filtrationthe active charcoal is filtered off through Celite
  4. customthe MeOH is removed under reduced pressure
  5. customThe residue is purified with flash chromatography

Sources & evidence

ORD record
ord-2e6203e63b6a4957add9950ca38ffcc2
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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