Hydrochloric Acid → HCID 15463562, compound

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Reaction Steps

To a 50 mL flask was added 0.300 g (0.889 mmol) of the 3-cyano derivative (Example 2) and 6 mL of 95% EtOH. The solution was stirred until homogeneous and then 1 mL of 6M NaOH and 1 mL of 30% hydrogen peroxide were added and the rxn was heated to reflux and allowed to stir for 3 h. Upon completion the reaction was cooled to rt and neutralized with conc. HCl. The solvent was evaporated in vacuo, and the crude residue was purified by column chromatography (Silica gel/Hexanes:Acetone 4:1) producing 0.20 g (63%) of the desired amide as a white solid. LRMS m/z (ESI) 356.2 (M+H)+ ; 1H-NMR (DMSO-d6, 300MHz) δ=8.74 (s, 1H), 8.32 (d, 1H, J=6.0 Hz), 8.10 (d, 1H, J=6.0 Hz), 7.66 (t, 1H, J=6.0 Hz), 7.48 (d, 4H, J=6.0 Hz), 7.33 (m, 6H).

Provenance & Evidence