Ammonium Chloride → HCID 178506220, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of {[6-(1-benzofuran-2-yl)-2-(trifluoromethyl)quinolin-4-yl]oxy}acetonitrile (0.200 g, 0.543 mmol) in DMF (10 mL) at room temperature was added sodium azide (0.177 g, 2.72 mmol) followed by NH4Cl (0.145 g, 2.72 mmol). The reaction was heated to 100° C. for 2 hours. The mixture was concentrated and diluted with 2 N HCl (˜5 mL). This mixture was stirred at room temperature for 1 hour. The solid which formed was filtered and then washed with excess H2O and hexane and dried under high vacuum to afford the product (0.173 g, 78%) as a yellow solid, mp>225° C. (dec.), mp>225° C. (dec.). Mass spectrum (+APCI, [M+H]+) m/z 412. 1H NMR (500 MHz, DMSO-d6): δ 15.44-17.96 (br s, 1H), 8.72 (d, 1H, J=2.0 Hz), 8.46 (dd, 1H, J=2.0, 9.0 Hz), 8.21 (d, 1H, J=8.8 Hz), 7.70-7.75 (m, 3H), 7.76 (s, 1H), 7.38 (t, 1H, J=7.7 Hz), 7.30 (t, 1H, J=7.9 Hz,), and 6.04 ppm (s, 2H). Elemental analysis for C20H12F3N5O2.0.5H2O: Calculated: C, 57.15; H, 3.12; N, 16.66. Found: C, 57.43; H, 2.72; N, 16.53.

Provenance & Evidence