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

HRID 470657Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([C:14](=[O:16])[CH3:15])[CH2:3]1>[Pd].C1COCC1>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:17])([CH3:1])[CH2:3][N:4]2[C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

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 %).

Workup

customThe slurry was degassed with vacuum/hydrogen three times
filtrationThe resulting mixture was filtered through a thin layer of Celite™
washthe cake was washed with THF (150 mL×2)
concentrationconcentrated in vacuo
additionfollowed by addition of toluene (150 mL)
customThe product was isolated by filtration
washthe wet cake was washed with D.I

Sources & evidence

ORD record: ord-8997aa8a611f40ccac6fef4c44cb6fd6
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629289B2

Reaction notes

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