Dibutyltin oxide → HCID 178497694, compound

Participants

Reaction Steps

A mixture of methyl 3-cyanobenzoate (320 mg, 1.98 mmol), dibutyltin oxide (49.7 mg, 0.20 mmol) and trimethylsilyl azide (0.54 mL, 3.96 mmol) in toluene (4.0 mL) was heated at reflux for 24 hours. The solvent was removed under reduced pressure and chased with methanol (1-2 mL). The residue obtained was flash chromatographed on silica gel eluting with acetic acid and methanol in methylene chloride to give the title compound (395.7 mg). 1H NMR (DMSO-d6, 300 MHz) δ3.0-4.5 (br, 1H), 3.92 (s, 3H), 7.75 (t, J=8 Hz, 1H), 8.11 (d, J=8 Hz, 1H), 8.32 (d, J=8 Hz, 1H), 8.54 (s, 1H). MS (DCl/NH3) m/e 205 (M+H)+, 222 (M+H+NH3)+.

Provenance & Evidence