1,2-Benzenedicarbonitrile, 4-nitro- → 1,2-Benzenedicarbonitrile, 4-amino-

HRID 634574

Reaction equation

HRID 634574 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9]

Participants

4

Reactant 1

HCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 925291,2-Benzenedicarbonitrile, 4-amino-Yield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A portion of 4-nitrophthalonitrile (5.15 g, 29.8 mmole) was dissolved in 125 mL methanol in a hydrogenation flask. The catalyst, 10% Pd/C (515 mg), was added to the mixture which was then flushed with H2 and stirred under 50 psi of H2 for 1 hour. The catalyst was removed by filtration and the solvent was distilled off under vacuum. The desired 4-aminophthalonitrile was obtained in 86% yield (3.66 g).

Workup

  1. customwas then flushed with H2
  2. customThe catalyst was removed by filtration
  3. distillationthe solvent was distilled off under vacuum

Sources & evidence

ORD record
ord-8c820d56c656418591e22241ec76bd51
Source dataset
uspto-grants-2001_02
Patent number
US06183727B2

Linked notes

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