1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone → 1-(6-Amino-3,3-dimethylindolin-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

1-(3,3-Dimethyl-6-nitroindoline-1y)ethanone (Example 5, 50 g), 5% Pd/C (1 g, 50% wet) and THF (200 mL) were charged to a 400 mL hydrogenation reactor. The slurry was degassed with vacuum/hydrogen three times and stirred for 6 h at 60° C. under hydrogen (30 PSI). The resulting mixture was filtered through a thin layer of Celite™ and the cake was washed with THF (150 mL×2). The filtrate and washes were combined and concentrated in vacuo, followed by addition of toluene (150 mL). The product was isolated by filtration and the wet cake was washed with D.I. water (100 mL×2) and 50 mL toluene to afford 1-(6-amino-3,3-dimethyl-indolin-1-yl)ethanone (38.5 g, 94% yield, >99.9 A %, 100 wt %).

Provenance & Evidence