Hydrochloric Acid → HCID 44626297, compound

Participants

Reaction Steps

To a solution of 2 (380 mg, 1.22 mmol) and hydroxylamine (50% in water, 1.25 mL) in a 1:1 THF:methanol (10 mL) was added base (KOH (275 mg, 4.9 mmol) or NaOH). The mixture was stirred at room temperature for 2 h, acidified to pH 7 with 1M HCl solution, diluted with ethyl acetate and washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was triturated with 50% ethyl acetate:hexanes, filtered, and rinsed with hexanes to afford compound 3 as a white solid (170 mg, 45%). 1H NMR (DMSO-d6) δ (ppm): 10.81 (br s, 1H), 8.88 (br s, 1H), 7.16 (d, J=1.0 Hz, 2H), 6.99 (dd, J=8.4, 1.8 Hz, 2H), 6.67 (d, J=8.1 Hz, 2H), 4.53-4.45 (m, 5H), 3.12 (t, J=8.6 Hz, 4H). LRMS (ESI): (calc) 311.1 (found) 310.3 (M)−.

Provenance & Evidence