Trimethyl((2-nitrophenyl)ethynyl)silane → HCID 57883359, compound

HRID 1817921Notes

Reaction equation

HRID 1817921 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O>CO.[Pd]>[CH3:14][Si:2]([CH3:1])([CH3:15])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]

Participants

4

Reactant 1

HCID 11333470Trimethyl((2-nitrophenyl)ethynyl)silane

Product 1

HCID 57883359HCID 57883359, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10.9 g (50 mmol) of trimethyl-(2-nitrophenylethynyl)silane were dissolved in 200 ml of methanol, and 0.5 g of palladium-on-carbon (5%) were added. The mixture was then hydrogenated in an autoclave at 4 bar for 12 h. Removal of the solvent and column-chromatographic purification on silica gel 60 (mobile phase: methylene chloride) gave 4.1 g of 2-(2-trimethylsilylethyl)phenylamine [log P (pH 2.3)=2.58].

Workup

  1. customRemoval of the solvent and column-chromatographic purification on silica gel 60 (mobile phase: methylene chloride)

Sources & evidence

ORD record
ord-d1119feb7f484e87805b6e04cb9b5057
Source dataset
uspto-grants-2009_10
Patent number
US07598389B2

Reaction notes

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