Tert-butyl 3-nitrobenzylcarbamate → tert-butyl N-((3-aminophenyl)methyl)carbamate

HRID 2366760Notes

Reaction equation

HRID 2366760 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 22620025Tert-butyl 3-nitrobenzylcarbamate

Product 1

HCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamateYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (3-nitrophenyl)methylcarbamate (40.5 g, 0.161 mol) in ethanol (810 mL) was added 10% palladium-carbon (4.1 g), and the mixture was stirred at room temperature for 19 hr under a hydrogen atmosphere. The insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The precipitate was collected by filtration to give the title compound (34.1 g, 96%) as a colorless powder.

Workup

  1. filtrationThe insoluble material was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ae562795c992411dac200f4ea61fac90
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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