反应详情

To a solution of 4-methyl-5-nitro-3-(3-hydroxypropyl)indole (0.365 g, 1.56 mmol) in 20 mL of absolute ethanol was added 10% palladium-on-charcoal (0.150 g) and the mixture was hydrogenated on a Parr shaker at 50 psi for 0.5 h. The mixture was then filtered through a plug of Celite, the catalyst was washed with additional ethanol and the filtrate was evaporated to give the title compound (0.280 g, 88%) as a solid. An analytical sample was crystallized from ethyl acetate to give cream-coloured needles, mp 141°-142° C.: IR (KBr) 3388, 3180, 1618 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ 10.20 (br s, 1H), 6.87 (d, J=8.8 Hz, 1H), 6.83 (s, 1H), 6.50 (d, J=8.3 Hz, 1H), 4.43 (t, J=5.2 Hz, 1H), 4.12 (s, 2H), 3.47 (dt, J=6.4, 5.3 Hz, 2H), 2.79 (t, J=7.7 Hz, 2H), 2.31 (s, 3H), 1.73 (m, 2H). Anal. Calcd for C12H16N2O: C, 70.55; H, 7.90; N, 13.72. Found: C, 70.41; H, 7.89; N, 13.55.

1. filtrationThe mixture was then filtered through a plug of Celite
2. washthe catalyst was washed with additional ethanol
3. customthe filtrate was evaporated