Tert-butyl 3-nitrophenylcarbamate → tert-butyl N-(3-aminophenyl)carbamate

HRID 56120Notes

Reaction equation

HRID 56120 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 10514065Tert-butyl 3-nitrophenylcarbamate

Product 1

HCID 12877220tert-butyl N-(3-aminophenyl)carbamateYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (3-nitrophenyl)carbamate (10.75 g, 45.12 mmol) in MeOH (150 mL) was added catalyst 10% Pd/C (0.48 g). The reaction mixture was stirred at rt under H2 overnight, and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as a pale yellow solid (7.59 g, 81%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

Sources & evidence

ORD record
ord-b7d28fe6615c44dea3918caae4f024f9
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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