Stannous Chloride → HCID 68153934, compound

Participants

Reaction Conditions

Reaction Steps

The procedure described for the preparation of 7 was repeated using 300 mg (1.15 mmol) of 8 in 20 mL of glacial HOAc and 1.85 g (9.76 mmol, 8.5 equiv) of SnCl2 in 3 mL of conc HCl to afford, after stirring ca. 12 h at 25° C. and quenching with water, a precipitate. The precipitate was collected by filtration, washed with 5 mL of glacial acetic acid and suspended in 80 mL of water. The aqueous suspension was adjusted to pH 9-10 with NaOH and was extracted with Et2O. The combined ethereal extracts were washed with water, dried over anhydrous MgSO4, and concentrated. The product was recrystallized from hexane to afford 220 mg (83%) of 9 as colorless crystals: mp 74-75° C. 1H NMR (DMSO-d6): δ 7.28 (d, 2H, J=8.8 Hz), 7.27-7.22 (m, 1H), 7.21 (d, 1H, J=16.8 Hz), 7.13-7.06 (m, 2H), 6.77 (d, 1H, J=16.8 Hz), 6.57 (d, 2H, J=8.8 Hz), 5.43 (s, 2H). 13C NMR (DMSO-d6): δ 160.35 (dd, J1=246.8 Hz, J2=8.0 Hz, two C), 150.06, 136.41 (t, J=7.9 Hz), 128.42 (two C), 127.99 (t, J=10.3 Hz), 124.68, 115.31 (t, J=15.1 Hz), 114.29 (two C), 112.33 (dd, J1=19.1 Hz, J2=6.3 Hz, two C), 108.84. MS: m/z (%) 232 (18), 231 (100), 183 (13). Anal. Calcd for C14H11F2N: C, 72.72; H, 4.79. Found: C, 72.77; H, 4.83.

Provenance & Evidence