Tert-butyl [3-(3-amino-4-nitrophenoxy)phenyl]carbamate → Tert-butyl [3-(3,4-diaminophenoxy)phenyl]carbamate

HRID 2190497Notes

Reaction equation

HRID 2190497 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[N+:23]([O-])=O)[O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][CH:11]=1>O1CCCC1.CO.[C].[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[NH2:23])[O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 1

HCID 86655409Tert-butyl [3-(3-amino-4-nitrophenoxy)phenyl]carbamate

Product 1

HCID 86655410Tert-butyl [3-(3,4-diaminophenoxy)phenyl]carbamateYield 105.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl [3-(3-amino-4-nitrophenoxy)phenyl]carbamate (5.51 g, 15.6 mmol) and 10% palladium-carbon (875 mg) were dissolved in tetrahydrofuran (20 mL) and methanol (100 mL), and the mixture was stirred at room temperature for 18 hr under a hydrogen atmosphere (3 atm). Palladium-carbon was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (5.17 g) as a purple amorphous substance.

Workup

  1. filtrationPalladium-carbon was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e62bdbe13dd84603b28ac83cf7213d1f
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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