(4-Methoxy-2-nitro-phenyl)-carbamic acid tert-butyl ester → tert-butyl N-(2-amino-4-methoxyphenyl)carbamate

HRID 658038Notes

Reaction equation

HRID 658038 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[N+:16]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[NH2:16])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10730597(4-Methoxy-2-nitro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 10752410tert-butyl N-(2-amino-4-methoxyphenyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (120 mg) was added to a solution of 4-methoxy-2-nitrophenylcarbamic acid t-butyl ester (Reference Compound No. 11-1, 1.3 g, 4.8 mmol) in methanol (20 mL), and then the reaction mixture was stirred under a hydrogen atmosphere at room temperature for 9 hours. The insoluble was filtered off, and then the solvent was evaporated under reduced pressure. The resulting solid was collected by filtration with hexane to give 1.1 g of the title reference compound as a pale brown solid quantitatively.

Workup

  1. filtrationThe insoluble was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. filtrationThe resulting solid was collected by filtration with hexane
  4. customto give 1.1 g of the title reference compound as a pale brown solid quantitatively

Sources & evidence

ORD record
ord-a2c4402f5f8e47a59bce5b4a0a4cb93e
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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