p-Toluidine → 4-Methoxy-4'-methyldiphenylamine

Participants

Reaction Conditions

Reaction Steps

Into a reactor were introduced 0.214 g (2.00 mmol) of p-toluidine and 4 mL of dioxane under a nitrogen atmosphere. The amine was dissolved in the solvent. To this solution were added 0.515 g (2.2 mol) of p-iodoanisole, 0.231 g (2.4 mmol) of sodium t-butoxide, 4.5 mg (1 mol % based on the amine) of palladium acetate, and 15.6 mg (2 mmol % based on the amine) of the 1,1-diphenyl-2-(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 8 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.351 g (82%) of N-p-methoxyphenyl-N-p-tolylamine as yellow crystals. The results obtained are shown in Table 20.

Provenance & Evidence