38753-50-3

29026-74-2

General procedure for the synthesis of 2-(1-methylethoxy)aniline from 1-isopropoxy-2-nitrobenzene: The product of Example 242A (5.00 g, 27.5 mmol) was dissolved in methanol, 10% Pd/C catalyst was added, and the catalytic hydrogenation reaction was carried out under hydrogen pressure (60 psi). Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 3.75 g (90% yield) of the target product 2-(1-methylethoxy)aniline in the form of a brown oil. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 1.35 (d, 6H, J = 6.1 Hz), 3.77 (br s, 2H), 4.52 (m, 1H), 6.75 (m, 4H); the mass spectrum (DCI/NH3) showed m/e 152 (M + H)+.