HCID 21914155, compound → 3-(4-Aminomethylphenyl)-4-methoxyaniline

HRID 1988309Notes

Reaction equation

HRID 1988309 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])=[CH:5][CH:4]=1.[H][H]>CO.[Pd]>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[NH2:15])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 21914155HCID 21914155, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 219141603-(4-Aminomethylphenyl)-4-methoxyaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(4-aminomethylphenyl)-4-nitroanisole (4.50 g) in methanol (200 mL) was treated with 10% palladium on carbon (200 mg). The reaction mixture was stirred under one atmosphere of hydrogen for 2.5 hours. The reaction mixture filtered through Celite, and the filter cake was washed with methanol (3×25 mL). The filtrate was concentrated to dryness and the residue was purified by flash chromatography on silica gel (80 g) eluting with 0-6% methanol/0.5% triethylamine/dichloromethane. Pure fractions were combined and concentrated to give 3-(4-aminomethylphenyl)-4-methoxyaniline as an off white powder.

Workup

  1. filtrationThe reaction mixture filtered through Celite
  2. washthe filter cake was washed with methanol (3×25 mL)
  3. concentrationThe filtrate was concentrated to dryness
  4. customthe residue was purified by flash chromatography on silica gel (80 g)
  5. washeluting with 0-6% methanol/0.5% triethylamine/dichloromethane
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed3a6f35e87f44a28b8a70ef1ae34328
Source dataset
uspto-grants-2009_06
Patent number
US07553971B2

Reaction notes

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