2-(4-Methoxy-phenyl)-vinyl-4-methyl-2-nitro-benzene → 2-[2-(4-Methoxy-phenyl)-ethyl]-5-methyl-phenylamine

HRID 607221Notes

Reaction equation

HRID 607221 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[N+:18]([O-])=O)=[CH:5][CH:4]=1.[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[NH2:18])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 866146232-(4-Methoxy-phenyl)-vinyl-4-methyl-2-nitro-benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 668082692-[2-(4-Methoxy-phenyl)-ethyl]-5-methyl-phenylamineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product from Example 106A (164 mg, 0.6 mmol) and 10% palladium on charcoal (50 mg) in ethanol (20 ml) was hydrogenated with a hydrogen balloon for three days. The solvent was filtered through celite, washed with ethanol and evaporated under vacuum to provide the title compound (140 mg, 97%).

Workup

  1. filtrationThe solvent was filtered through celite
  2. washwashed with ethanol
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-e9f6fd6c8c5c4b6aad6ea28423e4a7c3
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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