2-Bromo-6-nitrobenzonitrile → 2-Amino-6-bromobenzonitrile

HRID 631888Notes

Reaction equation

HRID 631888 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:3]=1[C:4]#[N:5]>CO.O1CCOCC1.[Fe]>[NH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 1

HCID 249719882-Bromo-6-nitrobenzonitrile

Product 1

HCID 98130382-Amino-6-bromobenzonitrileYield 87.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-6-nitrobenzonitrile (5 g) was dissolved in a solution of methanol (100 mL) and dioxane (65 mL) and heated to reflux. Iron powder (4.6 g) was added portion wise over 20 minutes and the mixture was heated at reflux for 4 hours. The mixture was allowed to cool to room temperature, filtered and the filtrate was evaporated under vacuum. The residue was triturated with water and the solid was collected by filtration to give the title compound as a light brown solid (3.8 g).

Workup

  1. temperatureheated to reflux
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 4 hours
  4. filtrationfiltered
  5. customthe filtrate was evaporated under vacuum
  6. customThe residue was triturated with water
  7. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-7e5fc548026c420f8e3014a1d94d21f3
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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