5-(Tert-butyldimethylsilyloxy)-2-phthalimido-1-nitrobenzene → 5-(Tert-butyldimethylsilyloxy)-2-phthalimidoaniline

HRID 395815Notes

Reaction equation

HRID 395815 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])=[C:13]([N+:15]([O-])=O)[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:18]2[C:19](=[O:28])[C:20]3=[CH:27][CH:26]=[CH:25][CH:24]=[C:21]3[C:22]2=[O:23])=[C:13]([CH:14]=1)[NH2:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 181744725-(Tert-butyldimethylsilyloxy)-2-phthalimido-1-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 181744945-(Tert-butyldimethylsilyloxy)-2-phthalimidoanilineYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-(tert-butyldimethylsilyloxy)-2-phthalimido-1-nitrobenzene (5.00 g, 12.5 mmol) and 10% palladium-on-carbon (2.5 g) in ethyl acetate (60 mL) was stirred under 1 atm of hydrogen for 16 h. The mixture was filtered through a pad of diatomaceous earth and concentrated in vacuo to yield 4.1 g (89%) of the title compound.

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c00665f62a2428faebe29f8a0010df9
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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