4-Methyl-3-nitrobenzonitrile → 3-Amino-4-methylbenzonitrile

HRID 2184230Notes

Reaction equation

HRID 2184230 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:7]#[N:8])([O-])=O.[H][H]>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:7]#[N:8]

Participants

5

Reactant 2

HCID 5893334-Methyl-3-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 70164283-Amino-4-methylbenzonitrileYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

120 g of 3-nitro-4-methylbenzonitrile were suspended in 1.2 l of EtOH and hydrogenated with 50 l of hydrogen at RT in the presence of 7 g of Pd/C (10%). After removal of the catalyst on Celite, the solvent was stripped off to result in 95 g of pure product (97%). 1H-NMR (DMSO-d6; δ in ppm): 7.1 (dd, 1H); 6.90 (d, 1H); 6.85 (dd, 1H); 5.35 (s, 2H, NH2); 2.15 (s, 3H)

Workup

  1. customAfter removal of the catalyst on Celite

Sources & evidence

ORD record
ord-affba657d34146b2802dc0f4f6d1d251
Source dataset
uspto-grants-2005_05
Patent number
US06900319B2

Reaction notes

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