4-Aminophenol → HCID 58533483, compound

Participants

Reaction Steps

In a 100-mL RBF was combined 2-(4-fluorophenylamino)benzoic acid (2.5 g, 11 mmol), HATU (4.9 g, 13 mmol), 4-aminophenol (1.0 g, 9.2 mmol), N-ethyl-N-isopropylpropan-2-amine (3.2 mL, 18 mmol), and DCM (23 mL, 9.2 mmol). The reaction mixture was allowed to stir at RT overnight and was then absorbed onto a loading cartridge and passed through an 80 g silica gel column using hexanes: EtOAc as eluent. Fractions containing pure product were concentrated in vacuo to afford 2-(4-fluorophenylamino)-N-(4-hydroxyphenyl)benzamide as a brown oil. The oil was triturated with CH2Cl2 and hexanes, and the resulting solid was filtered through a 0.45 μM membrane filter and rinsed with hexanes. 2-(4-fluorophenylamino)-N-(4-hydroxyphenyl)benzamide was isolated as a off-white solid. Calcd for C19H15FN2O2: [M]+=322. Found: [M+H]+=323.

Provenance & Evidence