3-(Ethylamino)-4-nitrobenzonitrile → 4-Amino-3-(ethylamino)benzonitrile

HRID 433019Notes

Reaction equation

HRID 433019 reaction equation
[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[C:7]#[N:8])[CH3:2]>C(O)C.[Pd]>[NH2:12][C:11]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[NH:3][CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 187607953-(Ethylamino)-4-nitrobenzonitrile

Product 1

HCID 223799044-Amino-3-(ethylamino)benzonitrileYield 31.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Ethylamino-4-nitro-benzonitrile (0.3 g) was diluted with ethanol (5 mL) and was treated with 10% palladium on carbon (Pd/C)(0.070 g). The mixture was then shaken in a hydrogenation shaker under an atmosphere of hydrogen (40 psi) for 30 minutes. The resulting mixture was filtered through diatomaceous earth and concentrated. Silica gel chromatography using 20% ethyl acetate in hexanes as eluent gave 4-amino-3-ethylamino-benzonitrile (0.08 g).

Workup

  1. filtrationThe resulting mixture was filtered through diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5a0669e5a32f4297a96d67c1c1c89684
Source dataset
uspto-grants-2003_12
Patent number
US06664395B2

Reaction notes

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