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

HRID 1858027Notes

Reaction equation

HRID 1858027 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-])=O>[Pd].C(OCC)(=O)C>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[NH2:1])[C:6]#[N:7]

Participants

4

Reactant 1

HCID 5959014-Amino-3-nitrobenzonitrile

Product 1

HCID 7372853,4-DiaminobenzonitrileYield 100,000%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising 4-amino-3-nitrobenzonitrile (5 g, 0.031 mmol) and palladium on carbon (500 mg, 10 wt %) and ethyl acetate (150 mL) in a Parr flask was hydrogenated for 60 minutes (45-50 psi), filtered over celite and concentrated to dryness to provide 3,4-diaminobenzonitrile (4.09 g, 0.031 mol) as a white solid; PB-CI/MS: 134=(MH+); 1H-NMR (300 Mhz, DMSO-d6): 4.81 (bs, 2H), 5.39 (bs, 2H), 6.494 (d, 1H), 6.703 (s, 1H), 6.723 (d, 1H).

Workup

  1. filtration(45-50 psi), filtered over celite and
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f1f029691e714e98a2d437613e5f1ace
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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