3,3-Dimethyl-1-(2-nitrophenyl)-2,3-dihydro-1H-indole → 2-(3,3-Dimethyl-2,3-dihydro-1H-indol-1-yl)aniline

HRID 2192219Notes

Reaction equation

HRID 2192219 reaction equation
[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)[CH2:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])[CH2:3]1

Participants

4

Reactant 1

HCID 593377113,3-Dimethyl-1-(2-nitrophenyl)-2,3-dihydro-1H-indole

Product 1

HCID 593377202-(3,3-Dimethyl-2,3-dihydro-1H-indol-1-yl)anilineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2d (123 mg, 0.458 mmol) in MeOH was added 10% Pd/C (20 mg). The reaction mixture was stirred at rt under H2 for 2 h. The catalyst was filtered through a cake of Celite® and the filtrate was evaporated under reduced pressure to afford 2e (80 mg, 75%) as a yellowish powder. MS (ES) m/z 239 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered through a cake of Celite®
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-538f7a3b7f9d4d768c82be9d9ce74f7f
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Reaction notes

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