3-(2-Fluoro-4-nitrophenoxy)-2,6-dimethyl-pyridine → 4-(2,6-Dimethyl-pyridin-3-yloxy)-3-fluoro-phenylamine

HRID 2176843

Reaction equation

HRID 2176843 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[C:6]([CH3:12])=[N:7][C:8]([CH3:11])=[CH:9][CH:10]=1>C(O)C.[Pd]>[CH3:12][C:6]1[C:5]([O:4][C:3]2[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:2]=2[F:1])=[CH:10][CH:9]=[C:8]([CH3:11])[N:7]=1

Participants

4

Reactant 1

HCID 592873193-(2-Fluoro-4-nitrophenoxy)-2,6-dimethyl-pyridine

Product 1

HCID 592873214-(2,6-Dimethyl-pyridin-3-yloxy)-3-fluoro-phenylamineYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of intermediate 9 (5.88 g, 22.44 mmol) in ethanol (200 ml) was hydrogenated at room temperature in the presence of palladium 10% on activated carbon (0.58 g) for 3 hours. The solids were filtered off and the filtrate was evaporated till dryness to yield intermediate 10 (5.20 g, >99%) that was used without further purification.

Workup

  1. filtrationThe solids were filtered off
  2. customthe filtrate was evaporated till dryness

Sources & evidence

ORD record
ord-06082289c222429badbd3e3a6515fc3e
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Linked notes

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