Tert-butyl 2-methoxy-5-nitrophenylcarbamate → tert-butyl N-(5-amino-2-methoxyphenyl)carbamate

HRID 1014228Notes

Reaction equation

HRID 1014228 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]>C(O)C.[Pd]>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:5]=1

Participants

4

Reactant 1

HCID 45790233Tert-butyl 2-methoxy-5-nitrophenylcarbamate

Product 1

HCID 22344747tert-butyl N-(5-amino-2-methoxyphenyl)carbamateYield 91.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1,1-dimethylethyl [2-(methyloxy)-5-nitrophenyl]carbamate (6 g, 22 mmol) in absolute ethanol (150 mL) was hydrogenated with 10% Pd/C (˜1.00 g, Lancaster) at 50 psi overnight. The catalyst was removed by vacuum filtration through a celite pad, rinsed with methanol, and filtrate was concentrated under reduced pressure to provide 1,1-dimethylethyl [5-amino-2-(methyloxy)phenyl]carbamate (4.8 g, 90%) as a tan solid. ESIMS (M+H)+=239.

Workup

  1. customThe catalyst was removed by vacuum filtration through a celite pad
  2. washrinsed with methanol, and filtrate
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-585c543811e642c08c3fded3ab78aa3e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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