1,2,4-Trimethyl-5-nitrobenzene → 2,4,5-Trimethylaniline

HRID 844439Notes

Reaction equation

HRID 844439 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[NH2:10]

Participants

4

Reactant 1

HCID 691301,2,4-Trimethyl-5-nitrobenzene

Product 1

HCID 87172,4,5-TrimethylanilineYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

19.70 g of 2,4,5-trimethylnitrobenzene are dissolved in 500 ml of ethanol and the solution is then hydrogenated at room temperature and pressure in the presence of 1 g of 5% Pd/C. The catalyst is filtered off on Celite® and the medium is then evaporated to give 15.67 g of the expected compound.

Workup

  1. customis then hydrogenated at room temperature
  2. filtrationThe catalyst is filtered off on Celite®
  3. customthe medium is then evaporated

Sources & evidence

ORD record
ord-2587545f4ab348df9337b2853650d7ab
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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