HCID 3328476, compound → 4-Methyl[1,1'-biphenyl]-2-amine

HRID 905154Notes

Reaction equation

HRID 905154 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([N+:14]([O-])=O)[CH:3]=1.[H][H]>C(O)C.[Pd]>[NH2:14][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 3328476HCID 3328476, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 125594574-Methyl[1,1'-biphenyl]-2-amineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 44 g (0.21 mol) of 2-nitro-4-methylbiphenyl prepared in Example 1 in 250 ml of ethanol was hydrogenated over 3.0 g of 5% palladium on carbon in a Parr shaker. The uptake of hydrogen stopped after 45 minutes, and the reaction mixture was filtered and concentrated to give 37 g (97%) of 2-amino-4-methylbiphenyl as a brown liquid. This material was distilled through a 15 cm Vigreaux column to give 33 g (87%) of pure 2-amino-4-methylbiphenyl as a colorless liquid, which turned brown on standing.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c1ef9e8898764ee1a52068add11fc6ce
Source dataset
uspto-grants-1983_12
Patent number
US04422979

Reaction notes

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