Methanol → 4-Fluoro-5-(4-methylpiperazin-1-yl)-2-nitroaniline

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Reaction Steps

The acetamide (25.0 g, 0.085 mol) (obtained in step 1 above) was dissolved in methanol (160 mL) and 6 M NaOH solution (42 nL) was added dropwise at ca 30° C. and stirred for 6 h. The mixture was cooled in an ice bath and water (300 mL) was added dropwise. The resultant precipitate was collected by filtration and dried to yield 2-nitro-4-fluoro-5-(4-methylpiperazin-1-yl)aniline (16.0 g, 75%) as a brown solid. mp 154-155° C.; IR (KBr) 3383, 1247 cm-1 ; 1H NMR (CDCl3 ) δ 2.32 (s, 3H, CH3), 2.54 (t, J=5.0 Hz, 4H, N(CH2)2), 3.24 (t, J=4.6 Hz, 4H, N(CH2)2, 6.02 (d, J=7.5 Hz, 1H), 6.12 (brs, 2H, NH2), 7.74 (d, J=14.0 Hz, 1H); Mass (m/z) 254 (M+.).

Provenance & Evidence