Hydroxyamine hydrochloride → 5-Hydroxy-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-4-carbaldehyde oxime

Participants

Reaction Steps

Compound 71 (0.029 g, 0.1 mmol) in EtOH/Pyr (1 mL/0.5 mL) was treated with NH2OH HCl (0.040 g, 0.58 mmol) and the mixture heated briefly to reflux (approximately 5 minutes) and allowed to cool and then the solution was partitioned between EtOAc and 2 N HCl aq and the organic layer was then washed with NaHCO3 aq, brine, dried over MgSO4, filtered, concentrated and triturated with CH2Cl2 to render 29 mg of the desired oxime: Mp=205° C. (dec.); 1H NMR (DMSO-d6) δ 11.1 (s, 1 H), 10.0 (s, 1 H), 9.90 (s, 1H), 8.53 (s, 1 H), 7.65 (d, 2 H, J=8.6 Hz), 7.39 (s, 1 H), 6.88 (d, 2 H, J=8.7 Hz), 6.47 (s, 1 H), 3.94 (s, 3 H); MS 300 (M+H)+.

Provenance & Evidence