2,3-Dichloro-1,4-dimethyl-5-nitrobenzene → 3,4-Dichloro-2,5-dimethylaniline

HRID 486992Notes

Reaction equation

HRID 486992 reaction equation
[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]([N+:10]([O-])=O)[CH:5]=[C:6]([CH3:9])[C:7]=1[Cl:8]>C(O)C.[Pd]>[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:5]=[C:6]([CH3:9])[C:7]=1[Cl:8])[NH2:10]

Participants

4

Reactant 1

HCID 137729272,3-Dichloro-1,4-dimethyl-5-nitrobenzene

Product 1

HCID 190968883,4-Dichloro-2,5-dimethylanilineYield 20%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.0 grams (0.03 mole) of 3,4-dichloro-2,5-dimethyl-1-nitrobenzene in 70 milliliters of ethanol was hydrogenated at room temperature at 50 psi in the presence of 0.25 gram of 10% palladium on activated carbon as a catalyst. Working up the reaction mixture gave 1.21 grams (0.006 mole) of 3,4-dichloro-2,5-dimethylaniline as a yellow solid having a melting point of 72° C.-76° C. NMR analysis of the product indicated the following:

Sources & evidence

ORD record
ord-f2253da694d1438984eb46bf13ed456a
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Reaction notes

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