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At atmospheric pressure and at 130-160 degrees C, primary aromatic amines (p-XC6H4NH2, X = H, Cl, NO2) are mono-N-alkylated in a single step, with symmetrical and asymmetrical dialkyl carbonates ROCOOR', R = Me, R' = MeO(CH2)2O(CH2)2; R = R' = Et; R = R' = benzyl; R = R' = allyl; R = Et, R' = MeO(CH2)2O(CH2)2, in the presence of a commercially available NaY faujasite. No solvents are required. Mono-N-alkyl anilines are obtained with a very high selectivity (90-97%), in good to excellent yields (68-94%), on a preparative scale. In the presence of triglyme as a solvent, the mono-N-alkyl selectivity is independent of concentration and polarity factors. The reaction probably takes place within the polar zeolite cavities, and through the combined effect of the dual acid-base properties of the catalyst.
Selva et al. (Sat,) studied this question.