Hydroxyamine hydrochloride → 2,3-Dichloro-N-{2-[formyl(Hydroxy)amino]ethyl}benzamide

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Reaction Steps

To a solution of 2,3-dichloro-N-(2-oxo-ethyl)-benzamide (33 g, 0.14 mol) in MeOH (500 mL) was added hydroxylamine hydrochloride (20 g, 0.28 mol) and sodium acetate (23.6 g, 0.28 mol). The mixture was stirred 1.5 h and the MeOH was removed in vacuo. The residue was partioned between saturated NaHCO3 (200 mL) and dichloromethane/MeOH (9:1; 100 mL). The aqueous layer was extracted (4×100 mL) with dichloromethane/MeOH (9:1). The combined organic extracts were washed with brine (50 mL), were dried (Na2SO4) and were concentrated to provide the title compound (34.3 g, 96%) as a 1:1 mixture of cis and trans isomers as a clear, pale brown oil. 1H NMR (400 MHz, CD3OD): δ 7.66 (m, 1H); 7.45 (m, 3H); 6.78 (t, j=4.1 Hz, 0.5H); 4.30 (d, j=4.1 Hz, 1H); 4.12 (d, j=5.3 Hz, 1H).

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