4-[2-(Tert-butyldiphenylsilyloxy)ethyl]nitrobenzene → 4-[2-(Tert-butyldiphenylsilyloxy)ethyl]phenylamine

HRID 1858304Notes

Reaction equation

HRID 1858304 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[Si:1]([O:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 221251124-[2-(Tert-butyldiphenylsilyloxy)ethyl]nitrobenzene

Product 1

HCID 221249944-[2-(Tert-butyldiphenylsilyloxy)ethyl]phenylamineYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6.5 g (16 mmol) 4-[2-(tert-butyldiphenylsilyloxy)ethyl]nitrobenzene in methanol (30 ml) containing 750 mg of 10% palladium on carbon was hydrogenated at room temperature and atmospheric pressure for 2 hours. The catalyst was removed by filtration and the solvent evaporated to give 5.7 g of 4-[2-(tert-butyldiphenylsilyloxy)ethyl]phenylamine as a colorless liquid. [Mass spectrum (ESI) MH+ =376].

Workup

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-d0bb3e578c134171811bbc8dfd49acb8
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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