Hydrochloric Acid → HCID 86035754, compound

Participants

Reaction Conditions

Reaction Steps

4-Hydroxycoumarin (3.0 mmol, 0.487 g) is dissolved in 10 mL of THF. Triphenylphosphine (3.15 mmol, 0.825 g) and 3-dimethylamino-propan-1-ol (3.15 mmol, 0.372 mL) is added and the solution is cooled to 0° C. DIAD (3.30 mmol, 0.647 g) is added dropwise at 0° C. The reaction is stirred 30 min. at 0° C then is allowed to warm to ambient temperature and is stirred overnight. The solvent is evaporated under reduced pressure, and a solution of anhydrous HCl/MeOH (prepared by adding ˜5 mL acetyl chloride dropwise to 100 mL MeOH) is added to the residue. Alternatively 4M HCl in dioxane may be used. The solvent is removed under reduced pressure and the residue is treated with Et2O. The resulting solid is filtered, is washed with Et2O, and is dried to afford the title compound as the hydrochloric acid salt (0.485g, 57%). 1H NMR (DMSO-d6, 300 MHz) δ 10.35 (1H, br s), 7.90 (1H, dd, J=1.25, 7.75 Hz), 7.68 (1H, m), 7.41 (2H, m), 5.92 (1H, s), 4.32 (2H, t, J=5.75 Hz), 3.27 (2H, m), 2.80 (6H, s), 2.25 (2H, m); MS (ESI, Pos.) calcd for C14H17NO3 m/z [M+H]=248.1, found 248.1.

Provenance & Evidence