tert-Butyl [2-(4-nitrophenoxy)ethyl]carbamate → tert-Butyl [2-(4-aminophenoxy)ethyl]carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
N-(tert-butoxycarbonyl)-2-(4-nitrophenoxy)ethylamine (5.91 g) was dissolved into methanol (200 ml) and subjected to hydrogeration reaction at ambient pressure by adding 10% palladium carbon catalyst (0.5 g). After completion of hydrogeration reaction, excess catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (5.07 g) as color-less oily substance. (1-3) N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (1.00 g) was dissolved into pyridine (5 ml) and 2,6-dimethoxybenzoic acid chloride (0.87 g) was added into the solution. After being stirred for one hour, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml). The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) followed by saturated sodium chloride (30 ml). Solvent was distilled out and residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1) to obtain 4′-[2-(tert-butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) as white powder.
Workup
- customsubjected to hydrogeration reaction at ambient pressure
- customAfter completion of hydrogeration reaction, excess catalyst
- customwas removed by filtration
- concentrationFiltrate was concentrated under vacuum
Sources & evidence
- ORD record
- ord-8781cd360db7461e947183ea65b06389
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300368B1
Reaction notes
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