4-Hydroxybenzyl Alcohol → HCID 178522925, compound

Participants

Reaction Conditions

Reaction Steps

N-((4-Chlorophenyl)methyl)-4-oxo-6,7,8-trifluoro-1-(2-(trimethylsilyl)ethoxy) methyl-3-quinolinecarboxamide (1.00 g) from Preparation No. 13 and 4-hydroxymethyl phenol (500 mg) are dissolved in DMF (20 mL). Sodium hydride (60% dispersion, 80 mg) is added and the mixture is heated to 140° C. for 1 h. The reaction mixture is allowed to cool to rt, is poured into sat. aq. ammonium chloride (100 mL), and is extracted with ethyl acetate (3×50 mL). The organic layer is washed with brine (10 mL), dried (MgSO4), and concentrated. The crude product is purified by column chromatography (heptane/ethyl acetate, 1/1; 1/5) followed by recrystallization to afford 145 mg of the title compound as a white solid.

Provenance & Evidence