Tert-butyl [3-methyl-3-(5-methyl-2-nitro-phenylamino)-butyl]-carbamate → Tert-butyl [3-(2-amino-5-methyl-phenylamino)-3-methyl-butyl]-carbamate

HRID 33366Notes

Reaction equation

HRID 33366 reaction equation
[CH3:1][C:2]([NH:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-])=O)([CH3:13])[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]>CO.[Pd]>[NH2:22][C:16]1[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=1[NH:14][C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:10])([CH3:9])[CH3:11]

Participants

4

Reactant 1

HCID 86603965Tert-butyl [3-methyl-3-(5-methyl-2-nitro-phenylamino)-butyl]-carbamate

Product 1

HCID 86603966Tert-butyl [3-(2-amino-5-methyl-phenylamino)-3-methyl-butyl]-carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4.71 g (14.0 mmol) tert-butyl [3-methyl-3-(5-methyl-2-nitro-phenylamino)-butyl]-carbamate are dissolved in 110 mL methanol and hydrogenated in the presence of 340 mg palladium on charcoal (10%) at ambient temperature. Then the catalyst is separated off and the solvent is distilled off. Brown solid. Yield: 3.72 g (87%); mass spectroscopy: [M+H]+=308.

Workup

  1. customThen the catalyst is separated off
  2. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-3d51a67019ed45deae01456005b89813
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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