2-{[Tert-butyl(dimethyl)silyl]oxy}-6-nitroaniline → 3-[(Tert-butyldimethylsilyl)oxy]benzene-1,2-diamine

HRID 1351996Notes

Reaction equation

HRID 1351996 reaction equation
[Si:1]([O:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[C:10]=1[NH2:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>O1CCCC1.[Pd]>[Si:1]([O:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:10]=1[NH2:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 597342682-{[Tert-butyl(dimethyl)silyl]oxy}-6-nitroaniline

Product 1

HCID 223857163-[(Tert-butyldimethylsilyl)oxy]benzene-1,2-diamineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[tert-butyl(dimethyl)silyl]oxy}-6-nitroaniline (8.5 g, 31.7 mmol) in tetrahydrofuran (100 mL) is added a 10% palladium on carbon (50% wet, 8.2 g), and the mixture is vigorously stirred under hydrogen atmosphere at room temperature for one hour. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (ethyl acetate/n-hexane=1/5, 1/3 and 1/1) to give the title compound as brown oil (6.95 g, yield: 92%).

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe obtained residue is purified by silica gel column chromatography (ethyl acetate/n-hexane=1/5, 1/3 and 1/1)

Sources & evidence

ORD record
ord-9830106ef2af45659464e69d9515e522
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

Loading…