2-Methyl-4-nitro-1-phenylbenzene → 2-Methyl[1,1'-biphenyl]-4-amine

HRID 1701009Notes

Reaction equation

HRID 1701009 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 1

HCID 143174152-Methyl-4-nitro-1-phenylbenzene

Product 1

HCID 443032-Methyl[1,1'-biphenyl]-4-amineYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-4-nitro-1-phenylbenzene (12.7 gm, 60 mmol) was dissolved in ethanol (260 mL) and hydrogenated over 10% palladium on charcoal (1.27gm) 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-2-methyl-1-phenylbenzene (10.49 gm, 95%) 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-357417fe7a5048a8b37c6347426b75c0
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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