Methanol → 5-(methyloxy)-1-[(methyloxy)acetyl]-2,3-dihydro-1H-indol-6-amine

Participants

Reaction Steps

A slurry of 5-(methyloxy)-1-[(methyloxy)acetyl]-6-nitro-2,3-dihydro-1H-indole (3.96 g, 14.87 mmol) and NiCl2 6H2O (1.061 g, 4.46 mmol) in THF (50 mL) and MeOH (100 mL) was treated with NaBH4 (1.69 g, 44.6 mmol) in small portions. After 5 minutes the reaction mixture was concentrated onto Celite and purified by silica gel chromatography using THF. The crude product was triturated using CH2Cl2 and Et2O to obtain 5-(methyloxy)-1-[(methyloxy)acetyl]-2,3-dihydro-1H-indol-6-amine as a white solid (884 mg, 25%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.98 (t, J=8.24 Hz, 2H), 3.34 (s, 3H), 3.71 (s, 3H), 3.93 (t, J=8.,33 Hz 2H), 4.12 (s, 2H), 4.67 s, 2H), 6.71 (s, 1H), 7.54 (s, 1H); ESIMS (M+H)+=237.4.

Provenance & Evidence