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

HRID 1279931Notes

Reaction equation

HRID 1279931 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>[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

3

Reactant 1

HCID 2315043-(4-Nitrophenyl)pyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

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 CH2C12 (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 int 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), 7.41 (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 int vacuo

Sources & evidence

ORD record
ord-880d2bcc296a4d0eb606cf4f8c3f457b
Source dataset
uspto-grants-2002_09
Patent number
US06448405B1

Reaction notes

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