5-[(3,5-Difluorobenzyl)oxy]-2-nitrobenzonitrile → 2-Amino-5-[(3,5-difluorobenzyl)oxy]benzonitrile

HRID 1803840Notes

Reaction equation

HRID 1803840 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N+:15]([O-])=O)=[C:11]([CH:14]=1)[C:12]#[N:13]>O1CCOCC1.[Pd]>[NH2:15][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]2[CH:18]=[C:19]([F:21])[CH:20]=[C:2]([F:1])[CH:3]=2)=[CH:14][C:11]=1[C:12]#[N:13]

Participants

4

Reactant 1

HCID 669962345-[(3,5-Difluorobenzyl)oxy]-2-nitrobenzonitrile

Product 1

HCID 669971222-Amino-5-[(3,5-difluorobenzyl)oxy]benzonitrileYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-[(3,5-difluorobenzyl)oxy]-2-nitrobenzonitrile (1 g, 3.44 mmol) and palladium 5% on carbon (150 mg) in 1,4-dioxane (20 mL) was treated under hydrogen atmosphere (40 psi) at room temperature. After 4 hours, the mixture was filtered on a celite pad and evaporated to dryness affording 770 mg (yield 86%) of the title compound.

Workup

  1. additionwas treated under hydrogen atmosphere (40 psi) at room temperature
  2. filtrationthe mixture was filtered on a celite pad
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-b179b42a8ac040858e07b67ccea978d0
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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