Pyridine → HCID 136334155, compound

Participants

Reaction Steps

To a 5 ml round bottom flask was added 4-(4-hydroxyphenyl)-1-benzothiophene-7-carbaldehyde (42.0 mg, 0.165 mmol), hydroxylamine hydrochloride (23 mg, 0.331 mmol), and anhydrous pyridine (0.027 ml, 0.331 mmol) in MeOH (1.0 ml) was brought to reflux for 1.5 h and then allowed to cool. The mixture was then diluted with ether, washed with water (2 ml) and the organic layer was dried over anhydrous Na2SO4 then passed through a silica plug. Concentration under reduced pressure produced 38 mg (85%) of product as white solid. Further purification by column chromatography (30% EtOAc-hexanes) afforded 22 mg of product suitable for analytical analysis: mp 229.5–230.5° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.92 (2H, d, J=8.4 Hz), 7.41 (3H, appt), 7.49 (1H, d, J=5.7 Hz), 7.59 (1H, d, J=7.6 Hz), 7.85 (1H, d, J=5.6 Hz), 8.49 (1H, s), 9.68 (1H, s), 11.62 (1H, s); MS (ESI) m/z 268 ([M−H]).

Provenance & Evidence