3-(4-Nitrophenyl)pyridine → 4-(Pyridin-3-yl)aniline

HRID 2121750Notes

Reaction equation

HRID 2121750 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O>C(Cl)Cl.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 2315043-(4-Nitrophenyl)pyridine

Product 1

HCID 4595224-(Pyridin-3-yl)anilineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flame-dried r.b. flask equipped with a magnetic stirring bar was dissolved 3-(4-nitrophenyl)pyridine (131 mg, 0.655 mmol) and 10% Pd on C (10 mg) in anhydrous CH2Cl2 (3mL) was added. The flask was repeatedly evacuated and filled with N2 to remove any residual O2, and then H2 gas was introduced. The solution was stirred at rt for 18 h, filtered though a Celite™ plug and concentrated in vacuo to give the desired amine (105 mg, 95%) as an off-white solid. Data for 3-(4-aminophenyl)pyridine: Rf=0.17 (silica gel, methanol/CHCl3, 5/95); 1H NMR (400 MHz, acetone-d6) 8.77 (d, J=2.3, 1H), 8.42 (dd, J=6.4, 1.6, 1H), 7.88 (m, 1H), 7.4 (d, J=8.5, 2H), 7.33 (m, 1H), 6.78 (d, J=8.5, 2H), 4.86 (br s, 2H).

Workup

  1. customflask equipped with a magnetic stirring bar
  2. additionwas added
  3. customThe flask was repeatedly evacuated
  4. additionfilled with N2
  5. customto remove any residual O2
  6. additionH2 gas was introduced
  7. filtrationfiltered though a Celite™ plug
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d8f23664c984d5b933cf71eb5f3bc96
Source dataset
uspto-grants-2004_02
Patent number
US06696459B1

Reaction notes

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