4-t-Butylamino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene → 4-Amino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene

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Reaction Steps

A solution of 2-{3-[(tert-butyl)amino]-2-fluoro-6-nitrophenyl}ethanol (3.9 g, 15 mmol), as prepared in the preceding step, in concentrated HCl (40 mL) was refluxed for 2 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate (6×50 mL). The extracts were combined, washed with saturated NaHCO3 (2 times) and brine, dried over Na2SO4, and concentrated to give the crude product as a solid. The solid was triturated in hexane, filtered, and dried in high vacuum to produce the title compound (2.8 g, 93% yield) as a yellow solid. 1H-NMR (400 MHz, CD3OD) δ 7.80 (dd, J=9.1, 1.5 Hz, 1H), 6.70 (t, J=9.0 Hz, 1H), 3.77 (t, J=7.1 Hz, 2H), 3.26 (dt, J=7.3, 2.8 Hz, 2).

Provenance & Evidence