Water → N-(3-hydroxypropyl)-2-anthraquinonecarboxamide

Participants

Reaction Steps

To a stirred suspension of anthraquinone-2-carboxylic acid (Aldrich, 10.00 g, 39.64 mmol) in DMF (130 ml), was added (benzotriazol-1-yloxy)tris(dimethylamino)-phosphonium hexafluorophosphate (17.54 g, 39.66 mmol) and trethylamine (11.05 ml, 79.28 mmol). The resulting mixture (initially a clear green solution) was stirred at room temperature for 10 min. before dropwise addition of 3-amino-1-propanol (3.34 ml, 43.67 mmol). The reaction mixture (clear brown solution) was stirred at room temperature in the dark for 17 hours. The solution was poured in a thin stream into water (300 ml) containing some ice. The precipitated material was isolated by filtration and recrystallised from boiling 96% ethanol (ca. 200 ml) and gave the title compound 2 as a bright yew solid (6.93 g, 57% yield).

Provenance & Evidence