Water → 5-(tert-Butyl)-2-methoxy-3-nitroaniline

HRID 2360512Notes

Reaction equation

HRID 2360512 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-])=O)[C:8]([O:14][CH3:15])=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.CC1CCC=CC1>C(O)C.[Pd].C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[C:7]([NH2:16])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 962WaterHCID 115724-Methylcyclohexene2×HCID 42526024-tert-Butyl-2,6-dinitroanisole

Product 1

HCID 112068635-(tert-Butyl)-2-methoxy-3-nitroaniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 g 5-tert-butyl-2-methoxy-1,3-dinitro-benzene are dissolved in 20 ml ethanol and combined with 2 ml of water and 100 mg of 10% palladium on charcoal. The mixture is refluxed, 1.9 ml of 4-methyl-1-cyclohexene are added and the mixture is refluxed for a further 2 hours. Then a further 1.0 ml of 4-methyl-1-cyclohexene are added dropwise and the mixture is refluxed for a further 16 hours. Then it is cooled to ambient temperature, the solvents are eliminated in vacuo and the residue is taken up in ethyl acetate. The mixture is washed with saturated aqueous sodium hydrogen carbonate solution, water, saturated aqueous sodium chloride solution and dried with sodium sulphate. The solvent is eliminated in vacuo and the product thus obtained is further reacted directly.

Workup

  1. temperatureThe mixture is refluxed
  2. temperaturethe mixture is refluxed for a further 2 hours
  3. temperaturethe mixture is refluxed for a further 16 hours
  4. washThe mixture is washed with saturated aqueous sodium hydrogen carbonate solution, water, saturated aqueous sodium chloride solution
  5. dry with materialdried with sodium sulphate
  6. customthe product thus obtained
  7. customis further reacted directly

Sources & evidence

ORD record
ord-6834b957faa846118be0c825c6794cb0
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

Loading…