Hydrochloric Acid → 4-Fluoro-5-(pyrrolidin-1-yl)-1,2-phenylenediamine

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Reaction Steps

The nitroaniline derivative (5.0 g, 0.022 mol) (obtained in step 1 above) was reduced using Fe powder (12.6 g, 0.22 mol), conc. HCl (33 mL) and ethanol (33 mL) as described in preparation 10 (step 2) to yield 4-fluoro-5-(pyrrolidin-1-yl)-1,2-phenylenediamine (4.2 g, 97%) as viscous oil. IR (Neat) 3340, 1524 cm-1 ; 1H NMR (CDCl3) δd 1.93 (m, 4H, (CH2)2), 3.24 (m, 4H, N(CH2)2), 3.56 (brs, 4H, 2×NH2), 6.18 (d, J=7.2 Hz, 1H), 6.48 (d, J=13.2 Hz, 1H); Mass (m/z) 195 (M+.).

Provenance & Evidence