2-Methyl-5-(2-methyl-4-nitrophenoxy)pyridine → 3-Methyl-4-((6-methylpyridin-3-yl)oxy)aniline

HRID 1292968Notes

Reaction equation

HRID 1292968 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[CH3:18])=[CH:4][N:3]=1.[H][H]>C(O)C.[Pd]>[CH3:18][C:10]1[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 179901022-Methyl-5-(2-methyl-4-nitrophenoxy)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)anilineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The solution of 2-Methyl-5-(2-methyl-4-nitro-phenoxy)-pyridine (6.4 g, 26.2 mmol), 10 wt % Pd/C (0.50 g) in ethanol (100 mL) was stirred under 1 atm hydrogen at rt for 24 h. Then the Pd/C catalyst was removed by filtration through a layer of celite. Removal of the solvent gave the desired product as an off-white solid (5.55 g, 99%). 1H-NMR (DMSO-d6) δ 8.04 (d, J=2.7 Hz, 1H), 7.13 (d, J=5.4 Hz, 1H), 7.02 (dd, J=8.7, 3.1 Hz, 1H), 6.68 (d, J=8.7 Hz, 1H), 6.49 (d, J=2.6 Hz, 1H), 6.42 (dd, J=8.4, 2.8 Hz, 1H), 4.96 (br, 2H), 2.39 (s, 3H), 1.97 (s, 3H). LCMS RT=1.04 min; [M+H]+=215.2.

Workup

  1. customThen the Pd/C catalyst was removed by filtration through a layer of celite
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-349680d153ea41b4a76b0e7c198319fb
Source dataset
uspto-grants-2007_07
Patent number
US07238701B2

Reaction notes

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