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

HRID 1584088Notes

Reaction equation

HRID 1584088 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 in the presence of 7 g of Pd/C (10%) with 50 l of hydrogen at room temperature. After removal of the catalyst, the solvent was stripped off. 95 g of pure product were obtained (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 [sic]); 2.15 (s, 3H)

Workup

  1. customAfter removal of the catalyst

Sources & evidence

ORD record
ord-a980da149f604ca99b736c0b58c7e830
Source dataset
uspto-grants-1999_08
Patent number
US05932567

Reaction notes

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