4-tert-Butyl-2,6-dinitrochlorobenzene → 2-Chloro-5-(1,1-dimethylethyl)-3-nitrobenzenamine
Reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[H][H]>CO>[Cl:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]([C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:6][C:7]=1[NH2:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 100 parts of 2-chloro-5-(1,1-dimethylethyl)-1,3-dinitrobenzene and 800 parts of methanol is hydrogenated at normal pressure and at room temperature with 10 parts of ruthenium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 69 parts (78%) of 2-chloro-5-(1,1-dimethylethyl)-3-nitrobenzenamine as a residue.