Ethanol → 1-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Participants

Reaction Steps

The solution of 1-acetyl-5-nitroindoline (1.0 g, 4.85 mmol) in ethanol-THF (100 mL: 30 mL) was hydrogenated over 5% Pd/C (600 mg) at atmosphere pressure for 2 h, filtered through Celite and concentrated in vacuo to give a white solid which was recrystalllized from ethanol. White crystalline solid (580 mg, 68%) was obtained. Mp 185-186.5° C. (lit 184-185° C., [21]); 1H NMR (270 MHz, DMSO): δ 7.73 (1H, d, J=8.6 Hz, ArH), 6.45 (1H, s broad, w1/2=1.8 Hz, ArH), 6.33 (1H, dd, J=8.6, 1.8 Hz, ArH), 4.82 (2H, s, NH2), 3.97 (2H, t, J=8.4 Hz, CH2), 2.99 (2H, t, J=8.4 Hz, CH2), 2.07 (3H, s, CH3); APCI-MS 175 (M−H+).

Provenance & Evidence