Pyridine → 890840-66-1

Participants

Reaction Steps

To a solution of Example 65A (415 mg, 2.14 mmol) in methanol (12 mL) was added methoxylamine hydrochloride (0.179 g, 2.14 mmol) and pyridine (0.87 mL, 10.8 mmol). The mixture was stirred overnight at room temperature and was then evaporated in vacuo. The residue was partitioned between ethyl acetate and H2O, and the organic layer was dried over Na2SO4 and was evaporated in vacuo. The residue thus obtained was dissolved in methanol (8 mL) and was hydrogenated (balloon) over 10% Pd-C in the presence of 4 drops of concentrated HCl overnight at room temperature. The catalyst was filtered off (Celite), and the filtrate was evaporated in vacuo. The residue was taken up in ether (20 mL) and was extracted with 1N HCl (3×10 mL). These acidic extracts were then basified to pH 10 with 2N NaOH and were extracted with ethyl acetate (3×10 mL). Drying over Na2SO4, followed by evaporation in vacuo, yielded Example 65B, 158 mg (48%). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.56 (m, 1H), 6.66 (m, 1H), 6.48 (m, 1H), 3.81 (m, 1H), 2.02 (m, 2H), 1.35 (s, 3H), 1.20 (s, 3H). MS (ESI) m/z 196 (M+H).

Provenance & Evidence