Hydrochloric Acid → HCID 86646223, compound

Participants

Reaction Steps

To the solution of 4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)benzonitrile (1 g, 3.98 mmol) in a mixed solvent of EtOH (100 mL) and THF (25 mL) under N2 was added Pd/C (10 wt. %, 0.169 g). The reaction mixture was hydrogenated with a H2 balloon at room temperature with stirring for 19 h. The mixture was filtered, rotary evaporated and purified by silica gel column eluted with MeOH containing 0.6% v. NH4OH (3 mL 28-30% NH4OH to 500 mL MeOH). The white solid obtained was dissolved in water (80 mL) and 6N HCl (2 mL) was added, filtered and the filtrate was freeze-dried to give the desired salt (4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)phenyl)methanaminium chloride as white solid (0.663 g, 2.27 mmol, yield 57.1%). M.p.>230° C. 1H NMR (DMSO-d6, 300 MHz): δ 9.23 (br. s, 1H), 8.38 (br. s, 3H), 7.49 (d, J=8.4 Hz, 2H), 7.43 (d, J=8.4 Hz, 1H), 7.31 (d, J=2.4 Hz, 1H), 7.16 (dd, J=8.1 & 2.4 Hz, 1H), 7.02 (d, J=8.4 Hz, 2H), 4.97 (s, 2H) and 3.97 (q, J=5.4 Hz, 2H) ppm. Purity (HPLC): 91.1% at 220 nm and 86.1% at 254 nm. MS: m/z=256 (M+1, ESI+) and m/z=254 (M−1, ESI−).

Provenance & Evidence