3-Amino-4-nitrobenzonitrile → 3,4-Diaminobenzonitrile

HRID 325065Notes

Reaction equation

HRID 325065 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[C:5]#[N:6].[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6]

Participants

5

Reactant 2

HCID 114919823-Amino-4-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 7372853,4-DiaminobenzonitrileYield 203.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Amino-4-nitrobenzonitrile (20.00 g, 0.042 mol) was hydrogenated under 50 psi of hydrogen gas in 250 mL of anhydrous ethanol with 1.00 g of 10% Pd/C for 5 hours. The mixture was then filtered through a pad of celite and the filtrate concentrated. Trituration of the resulting solid with diethyl ether afforded 11.40 g of the desired product as a tan solid (70%).

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-1ae41d8cb9774a218b26b75480af42e6
Source dataset
uspto-grants-2001_04
Patent number
US06221914B1

Reaction notes

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