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

HRID 2290052Notes

Reaction equation

HRID 2290052 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 mangetic 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 mangetic 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-160f88063b6f48aca30563a18c65c85d
Source dataset
uspto-grants-2000_07
Patent number
US06093821

Reaction notes

Loading…