4-Methoxy-3-(2-methoxyethoxy)nitrobenzene → 4-Methoxy-3-(2-methoxyethoxy)aniline

HRID 393604Notes

Reaction equation

HRID 393604 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][O:15][CH3:16]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][O:15][CH3:16]

Participants

4

Reactant 1

HCID 107993054-Methoxy-3-(2-methoxyethoxy)nitrobenzene

Product 1

HCID 108455954-Methoxy-3-(2-methoxyethoxy)anilineYield 103.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methoxy-3-(2-methoxyethoxy)nitrobenzene (7 g, 30 mmol) and 10% palladium-on-charcoal catalyst (1.4 g) in ethyl acetate (70 ml) was stirred under hydrogen at 3.3 atmospheres pressure for 1 hour. The catalyst was removed by filtration through diatomaceous earth and the solvent removed by evaporation. The solid residue was suspended in ethyl acetate, collected by filtration and dried under vacuum to give 4-methoxy-3-(2-methoxyethoxy)aniline (6.1 g, 100%).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe solvent removed by evaporation
  3. filtrationcollected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-aadfa82b400f4cbfbc72208da66c4116
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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