2-Amino-4-methylphenol → HCID 59297268, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 9,9-dipropyl-3-methoxyfluorene-2,7-dicarboxylic acid (43 g, 0.117 mol), thionyl chloride (30.0 mL, 48.9 g, 0.41 mol), p-dioxane (430 mL) and N-methylpyrrolidinone (2.0 mL), under argon, was stirred and heated under reflux for 3 h. Concentration of the reaction mixture by distillation of p-dioxane (50.0 mL) precipitated the diacid dichloride intermediate. The dark diacid dichloride solution, over a period of 20 min., was added to a cooled (0° C.) stirred solution of 2-amino-4-methylphenol (30.8 g, 0.25 mol), anhydrous piperidine (21.0 mL) and p-dioxane (200 mL) under argon. The resulting mixture was stirred at room temperature for 18 h then treated with water (50.0 mL) to dissolve the pyridinium chloride. The mixture was then added to 1.8 L of water, with stirring, to form the crude product as a granular solid, which was collected, washed with 50% methanol/water (500 mL), and dried to afford N,N′-bis(2-hydroxy-5-methylphenyl)-9,9-dipropyl-3-methoxyfluorene-2,7-dicarboxamide (77.2 g).

Provenance & Evidence