4-Methoxy-3-(2-methoxyethoxy)nitrobenzene → 4-Methoxy-3-(2-methoxyethoxy)aniline
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
Product 1
Reagents, catalysts & solvents 2
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%).