4-Fluoro-5-(4-methylpiperazin-1-yl)-2-nitroaniline → 4-Fluoro-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine

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Reaction Steps

21.2 g of 4-fluoro-5-(4-methylpiperazin-1-yl)-2-nitrophenylamine in solution in 800 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 2.1 g of palladium-on-charcoal at 25° C. for 16 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. 18.7 g of 4-fluoro-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine in the form of a black oil are isolated. 1H NMR (400 MHz, DMSO-d6, δ in ppm), for this batch, all the signals are broad with: 2.19 (s, 3H); 2.40 (m, 4H); 2.79 (m, 4H); 4.22 (s, 2H); 4.31 (s, 2H); from 6.24 to 6.33 (m, 2H). EI mass spectrum: m/z=224: M+. (base peak)—m/z=209: (M—CH3)+—m/z=153: (M−C4H9N)+—m/z=70: C4H8N+—m/z=43: C2H5N+.

Provenance & Evidence