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

HRID 877095Notes

Reaction equation

HRID 877095 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1>CO.[Pd]>[CH3:11][C:8]1[N:9]=[CH:10][C:5]([O:4][C:3]2[CH:12]=[CH:13][C:14]([NH2:16])=[CH:15][C:2]=2[CH3:1])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 179901022-Methyl-5-(2-methyl-4-nitrophenoxy)pyridine2×

Product 1

HCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-(2-methyl-4-nitrophenoxy)-2-methylpyridine (compound 12.1) (5 g) in methanol (50 mL) with palladium on carbon (10%, 300 mg) was hydrogenated on a Parr shaker for 24 hours at 60 psi. The mixture was filtered through Celite and all solvents were removed under reduced pressure to give a white crystalline solid, which was used without further purification. LCMS ESI(+) m/z: 215 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customall solvents were removed under reduced pressure
  3. customto give a white crystalline solid, which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-1d93452921224dfd9805d6da2f032a37
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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