1-(3-Methoxyphenyl)-2-methyl-4-nitrobenzene → 3'-Methoxy-2-methyl[1,1'-biphenyl]-4-amine

HRID 1700994Notes

Reaction equation

HRID 1700994 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[CH3:18])[CH:6]=[CH:7][CH:8]=1>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[C:10]([CH3:18])[CH:11]=1

Participants

5

Reactant 1

HCID 183192671-(3-Methoxyphenyl)-2-methyl-4-nitrobenzene

Product 1

HCID 183192763'-Methoxy-2-methyl[1,1'-biphenyl]-4-amineYield 101.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Methoxyphenyl)-2-methyl-4-nitrobenzene(23.4 gm, 96 mmol) was dissolved in a mixture of ethanol and ethyl acetate (3:1, 470 mL) and hydrogenated over 10% palladium on charcoal (2.3 gm) at 3 bar and 20° C. for 2 h. The mixture was filtered through Arbocel filter aid, washing with ethyl acetate. The filtrate was concentrated under reduced pressure to give 4-amino-1-(3-methoxyphenyl)-2-methylbenzene (20.8 gm, 100%) as a pinkish-brown oil.

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. washwashing with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-544499cdf0db4c6584696bfc69c32a30
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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