tert-Butyldimethyl(4-nitrophenoxy)silane → 4-((Tert-butyldimethylsilyl)oxy)aniline

HRID 1419926Notes

Reaction equation

HRID 1419926 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 532659tert-Butyldimethyl(4-nitrophenoxy)silane

Product 1

HCID 117155534-((Tert-butyldimethylsilyl)oxy)anilineYield 987.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

tert-Butyl-dimethyl-(4-nitro-phenoxy)-silane (7.3 g, 2.9 mmol) was dissolved in MeOH (75 ml) and hydrogenated in the presence of Pd on C (10%, E 101 N/D) at room temperature and atmospheric pressure for 1 hour. The catalyst was filtered and the solvent was evaporated to provide 4-(tert-Butyl-dimethyl-silanyloxy)-phenylamine (6.4 g, 99%) as light yellow oil, MS: m/e=223 (M+).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4f9efee849d54062a00c4c5e8ae3141e
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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