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

HRID 1864330Notes

Reaction equation

HRID 1864330 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>[Pd].C(OCC)(=O)C.C(O)C>[CH3:18][C:10]1[CH:11]=[C:12]([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)[NH2:15]

Participants

5

Reactant 1

HCID 179901022-Methyl-5-(2-methyl-4-nitrophenoxy)pyridine

Product 1

HCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)anilineYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-methyl-5-(2-methyl-4-nitrophenoxy)pyridine (141 g, 0.58 mol) and 10% palladium on charcoal (13 g) in ethyl acetate (200 ml) and ethanol (700 ml) was stirred under an atmosphere of hydrogen (1.2 bar) for 5 hours. After reaction completion, the mixture was purged with nitrogen and the catalyst was filtered off. The filtrate was evaporated to dryness to give 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (120.6 g, 98%) as a white solid; Mass spectrum MH+ 215.

Workup

  1. customAfter reaction completion
  2. customthe mixture was purged with nitrogen
  3. filtrationthe catalyst was filtered off
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-50d22c48aa9846feacf39883ddce3406
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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