Ethanol → 4,5-Dimethyl-1,2-phenylenediamine

HRID 1857412Notes

Reaction equation

HRID 1857412 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7](C)[C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[CH2:13](O)C>[Pd]>[NH2:6][C:5]1[CH:7]=[C:8]([CH3:13])[C:2]([CH3:1])=[CH:3][C:4]=1[NH2:10]

Participants

4

Reactant 2

HCID 702EthanolHCID 742196-Nitro-2,4-xylidine

Product 1

HCID 766354,5-Dimethyl-1,2-phenylenediamineYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 4,6-dimethyl-2-nitroaniline (1.66 g, 10.0 mmole) and 10% Pd/C (200 mg) in ethanol (35 mL) was hydrogenated for 2 h at room temperature under 25 psi H2. The catalyst was removed by filtration with celite and the solvent was removed by rota-evaporation to give 1.300 g (96%) of 1,2-diamino-4,5-dimethylbenzene as a brown solid. 1H NMR (CDCl3): 6.449 (s, 1 H), 6.469 (s, 1 H), 3.327 (br, 2 H), 3.259 (br, 2 H), 2.190 (s, 3 H), 2.159 (s, 3 H).

Workup

  1. customThe catalyst was removed by filtration with celite
  2. customthe solvent was removed by rota-evaporation

Sources & evidence

ORD record
ord-1c873020b0ab41919391e8f8c9461567
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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