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

HRID 2103078Notes

Reaction equation

HRID 2103078 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([N+:10]([O-])=O)=[CH:5][C:4]=1[CH3:13]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[CH:5][C:6]([NH2:10])=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 1

HCID 1398352-Methoxy-1,3-dimethyl-5-nitrobenzene

Product 1

HCID 41660974-Methoxy-3,5-dimethylanilineYield 81.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-methoxy-1,3-dimethyl-5-nitrobenzene (12 g) in ethanol in a Parr hydrogenation bottle, was added Pd/C (0.24 g, 10%). The mixture was shaken at 50 psi of H2 in the hydrogenator overnight. The reaction mixture was filtered through Celite® and the solvent was removed by evaporation. The crude residue was purified by column chromatography (10% ethyl acetate/hexane), giving 4-methoxy-3,5-dimethylaniline as a light yellow solid (8.2 g). 1H-NMR (300 MHz, CDCl3) δ=6.18 (s, 1H), 3.711 (s, 3H), 2.29 (s, 6H) ppm. MS: m/z 152 (100, M+H)+

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. customthe solvent was removed by evaporation
  3. customThe crude residue was purified by column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a53a4408c85f4bd2bb29a22f11f748f3
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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