Hydroxyamine hydrochloride → A-967079

Participants

Reaction Steps

To a solution of Example 1D (1.96 g, 10.2 mmol) in pyridine (40 mL) was added hydroxylamine hydrochloride (1.06 g, 15.3 mmol) in one portion. The reaction was stirred at ambient temperature for 12 hr, and then concentrated in vacuo. The residue was partitioned between EtOAc and 1M aq HCl. The separated organic phase was washed with 1M aq HCl and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; 5% to 30% EtOAc/hexanes; SF40-115 g column) and the late eluting component was isolated to afford the title compound as a white solid (0.16 g, 7.6% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 10.34 (s, 1H), 7.44-7.34 (m, 2H), 7.25-7.15 (m, 2H), 6.36 (s, 1H), 2.36 (q, J=7.4 Hz, 2H), 1.98 (d, J=1.5 Hz, 3H), 1.05 (t, J=7.4 Hz, 3H). MS (DCI+): 208 (M+H).

Provenance & Evidence