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

HRID 1600739Notes

Reaction equation

HRID 1600739 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, 1H), 6.469 (s, 1H), 3.327 (br, 2H), 3.259 (br, 2H), 2.190 (s, 3H), 2.159 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-90b2ed3e5edd45ae8e72813431357aae
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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