4-Aminophenol → HCID 118372886, compound

Participants

Reaction Steps

Into a 250 mL round bottom flask equipped with stir bar, condenser and nitrogen inlet was charged 2,6-bis(2-cyano-3-fluorophenoxy)benzonitrile (8.00 g, 21.4 mmol), 4-aminophenol (2.34 g, 21.4 mmol), potassium carbonate (3.56 g, 25.8 mmol) and N-methyl-1-pyrrolidone (NMP, 140 mL). The mixture was stirred at 100° C. for 24 hours until GC/MS showed no remaining reactant. It was allowed to cool to room temperature, followed by the addition of 3-aminophenol (2.34 g, 21.4 mmol) and potassium carbonate (3.56 g, 25.8 mmol). The mixture was stirred at 100° C. for 24 hours until GC/MS showed no remaining reactant. It was filtered and then the filtrate was poured into about 500 mL of saturated NaCl aqueous solution, followed by extraction with ethyl acetate (3×500 mL). The organic layer was combined and washed with distilled water (3×500 mL). It was then dried over sodium sulfate and filtered. Carbon black was added to the solution, which was then stirred at 65° C. for 30 minutes. It was passed through a Celite filter to remove carbon, and the solvent was removed by a rotary evaporator. A small amount of NMP residue in the product was removed by refluxing it in ethanol (75 mL). Product was collected by filtration and dried overnight at 80° C. in a vacuum oven to afford 5.73 g (48.5%) of a beige solid, m.p. 196.2-197.8° C. 1H-NMR (DMSO-d6): 5.16 (s, 2H, Ar—H), 5.37 (s, 2H, Ar—H), 6.29-6.31 (dd, 1H, Ar—H), 6.34-6.35 (t, 1H, Ar—H), 6.46-6.47 (dd, 1H, Ar—H), 6.60-6.65 (m, 3H, Ar—H), 6.78-6.80 (d, 1H, Ar—H), 6.88-6.93 (t, 3H, Ar—H), 6.96-6.98 (d, 1H, Ar—H), 7.07-7.15 (m, 3H, Ar—H), 7.58-7.62 (t, 1H, Ar—H), 7.64-7.68 (t, 1H, Ar—H), 7.78-7.80 (t, 1H, Ar—H). Elemental analysis: Calcd: C, 71.86; H, 3.84; N, 12.70. Found: C, 71.50; H, 3.87; N, 12.64.

Provenance & Evidence