2,4-Difluoro-5-nitrobenzonitrile → 5-Amino-2,4-difluorobenzonitrile

HRID 921782Notes

Reaction equation

HRID 921782 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5]>CO.[Pd]>[NH2:11][C:7]1[C:8]([F:10])=[CH:9][C:2]([F:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

4

Reactant 1

HCID 118197152,4-Difluoro-5-nitrobenzonitrile

Product 1

HCID 668484065-Amino-2,4-difluorobenzonitrileYield 70.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2,4-difluoro-5-nitrobenzonitrile (1.0 g, 5.43 mmol) and Pd/C 10% (0.1 g, 0.94 mmol) in MeOH (20 mL) was hydrogenated (balloon) for 5 hr. This was filtered and the solvent was removed. Flash chromatography on silica gel eluting with hexane containing 20% EtOAc gave 5-amino-2,4-difluorobenzonitrile (0.59 g) as a light yellow solid.

Workup

  1. customfor 5 hr
  2. filtrationThis was filtered
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-3bd5255189934367b37a35f73a949d36
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

Loading…