Stannous Chloride → HCID 10265481, compound

Participants

Reaction Steps

To a yellow solution of compound 10 (200 mg, 0.65 mmol) in CH3OH (4 mL) and conc. HCl (2 mL), SnCl2 (0–3 g) was added. The mixture was stirred at room temperature overnight and the solvent was evaporated to dryness. Water (15 mL) was added to the residue and the mixture was extracted with ethyl acetate (10 mL×3). The organic layer was discarded and the aqueous layer was adjusted to pH 10 with 1 N NaOH. The cloudy solution was extracted with ethyl acetate (10 mL×3). The combined organic layer was dried over Na2SO4 and the solvent was evaporated in vacuo to dryness. The residue was purified by column chromatography (silica gel, CH2Cl2/CH3OH, 95/5) to yield compound 12 as a white solid (77 mg, 42.7%), Rf=0.3 (silica gel, CH2Cl2/CH3OH, 90/10), mp 56–58° C.; 1H NMR (CDCl3) δ 7.40–7.49 (m, 1H), 7.18–7.25 (m, 1H), 7.05–7.13 (m, 2H), 6.84–6.93) (m, 1H), 6.38–6.48 (m, 2H), 4.74 (s, b, 2H), 3.57 (s, 2H), 2.31 (s, 6H). Anal. Calcd for C15H17FN2S: C, 65.19; H, 6.20; N, 10.14. Found: C, 65.06; H, 6.23; N, 10.04.

Provenance & Evidence