[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14]C)=[C:10]([N+:16]([O-])=O)[CH:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1.[H][H].[CH2:21](O)C>[Ni]>[N:1]1([CH:6]([C:8]2[CH:9]=[C:10]([NH:16][CH3:21])[C:11]([NH2:14])=[CH:12][CH:13]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1(b-1) A mixture of 21 parts of 4-[1-(1H-imidazol-1-yl)ethyl]-N-methyl-2-nitrobenzenamine and 160 parts of ethanol was hydrogenated at room temperature in a Parr apparatus at 0.5 105Pa with 20 parts of Raney-nickel catalyst. After the calculated amount of hydrogen was taken up, nitrogen was bubbled through the mixture and the catalyst was filtered off over diatomaceous earth. The filtrate was evaporated at <40° C., yielding 18.5 parts (100%) of 4-[1-(1H-imidazol-1-yl)ethyl]-N2 -methyl-1,2-benzenediamine as a residue (int. 97).
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