N,N-Diethyl-3-fluoro-4-nitrobenzamide → 3-Amino-N,N-diethyl-4-nitrobenzamide

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Reaction Steps

N,N-Diethyl-3-fluoro-4-nitro-benzamide (5.1 g, 21.2 mmol) was refluxed in a 2:1 mixture of NH4OH/EtOH (150 mL) for 48 h. The solution was cooled to rt and the solvent concentrated. The solution was then extracted (3×) with EtOAc. The combined organic phases were washed with brine and dried over anhydrous MgSO4. The crude product was crystallized from EtOAc/hexanes to give the title compound (4.35 g, 86% yield). 1H NMR (400 MHz, CD3OD) δ 8.12 (d, J=8.8 Hz, 1H), 6.92 (s, 1H), 6.56 (d, J=8.8 Hz, 1H), 3.51 (q, J=7.2 Hz, 2H), 3.28 (m, 2H), 1.23 (t, J=7.2 Hz, 3H), 1.13 (t, J=7.2 Hz, 3H).

Provenance & Evidence