tert-Butyl (4-methyl-3-nitrophenyl)carbamate → 5-(Boc-amino)-2-methylaniline

HRID 1184837Notes

Reaction equation

HRID 1184837 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18954623tert-Butyl (4-methyl-3-nitrophenyl)carbamate

Product 1

HCID 246997865-(Boc-amino)-2-methylanilineYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium on charcoal (6 g) was added to a solution of (4-methyl-3-nitro-phenyl)-carbamic acid tert-butyl ester 26 (60 g, 238 mmol) in ethanol (1200 mL). The mixture was hydrogenated at atmospheric pressure at room temperature for 18 h. The palladium catalyst was removed by filtration over celite and the solvent was removed by evaporation to give (3-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester 27 (51 g, 96%).

Workup

  1. customThe palladium catalyst was removed by filtration over celite
  2. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-f2c75e4c4dce4a608de3c7a36308b3b2
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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