2-(2-Methoxy-4-nitrophenyl)pyridine → 3-Methoxy-4-pyridin-2-ylaniline

HRID 2213096Notes

Reaction equation

HRID 2213096 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[NH2:9]

Participants

4

Reactant 1

HCID 219565262-(2-Methoxy-4-nitrophenyl)pyridine

Product 1

HCID 219565203-Methoxy-4-pyridin-2-ylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of Pd/C (0.25 g of 10%) in MeOH (5 mL) was mixed with a solution of 2-(2-methoxy-4-nitrophenyl)pyridine (0.5 g, 2.17 mmol) in MeOH (5 mL). The resulting reaction mixture was stirred vigorously for 12 h under an atmosphere of hydrogen, filtered through a pad of celite, and the filtrate was concentrated and purified by flash column chromatography on silica gel with EtOAc:hexanes (1:9 to 3:2) to afford 3-methoxy-4-pyridin-2-ylaniline.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered through a pad of celite
  3. concentrationthe filtrate was concentrated
  4. custompurified by flash column chromatography on silica gel with EtOAc:hexanes (1:9 to 3:2)

Sources & evidence

ORD record
ord-d5dd5503c3804078aab93600d49383f2
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

Loading…