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

HRID 1954521Notes

Reaction equation

HRID 1954521 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 (3 mL) 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, 1 H), 8.42 (dd, J=6.4, 1.6, 1 H), 7.88 (m, 1 H), 7.41 (d, J=8.5, 2 H), 7.33 (m, 1 H), 6.78 (d, J=8.5, 2 H), 4.86 (br s, 2 H).

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-7e0e69c092fc4c3a9b9f7ded1b069bd4
Source dataset
uspto-grants-2000_09
Patent number
US06121450

Reaction notes

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