Pyridine → HCID 136274568, compound

Participants

Reaction Steps

A mixture of 4-[4-(tert-butyldimethylsilanyloxy)-phenyl]-naphthalene-1-carbaldehyde (510 mg, 1.40 mmol), hydroxylamine hydrochloride (196 mg, 2.82 mmol), and anhydrous pyridine (0.228 ml, 2.82 mmol) in MeOH (3.2 ml) was heated to reflux for 3 h. The mixture was then concentrated under reduced pressure and dissolved in ether (5 ml). Then 1.0 M TBAF in THF (5.1 ml, 4.2 mmol) was added and stirred for 5 minutes. To the reaction was added water (5 ml) and then extracted with EtOAc. The organics were dried over anhydrous Na2SO4 and passed through a silica plug. Evaporation of the solvent and purification by column chromatography (10% MeOH-EtOAc) afforded 150 mg (41%) of product as a white solid: mp 200.0–200.5° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.93 (2H, d, J=8.0 Hz), 7.29 (2H, d, J=8.0 Hz), 7.42 (1H, d, J=7.3 Hz), 7.54 (1H, appt, J=7.6 Hz). 7.61 (1H, appt, J=7.6 Hz), 7.83 (1H, d, J=7.3), 7.92 (1H, d, J=8.4 Hz), 8.73 (1H, d, J=8.4 Hz), 8.81 (1H, s), 9.66 (1H,s), 11.45 (1H, s); MS (ESI) m/z 262 ([M−H]−).

Provenance & Evidence