4'-Fluoro-2'-methoxy-4-nitrobiphenyl → 4'-Fluoro-2'-methoxy[1,1'-biphenyl]-4-amine

HRID 442267Notes

Reaction equation

HRID 442267 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[C:4]([O:17][CH3:18])[CH:3]=1.[H][H]>[Pd].C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[C:4]([O:17][CH3:18])[CH:3]=1

Participants

5

Reactant 2

HCID 214164654'-Fluoro-2'-methoxy-4-nitrobiphenylHCID 178418361HCID 178418361, compound

Product 1

HCID 214164544'-Fluoro-2'-methoxy[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10 grams of 4'-fluoro-2'-methoxy-4-nitrobiphenyl in 250 ml. of ethanol is reduced by hydrogen at atmospheric pressure and at room temperature using 5% palladium-on-charcoal (0.5 gram) catalyst. After the required uptake of hydrogen, the mixture is filtered and the catalyst washed with fresh ethanol. The ethanol solution is then concentrated in vacuo, and the residue recrystallized from aqueous ethanol to yield 4-(4'-fluoro-2'-methoxyphenyl)-aniline.

Workup

  1. filtrationAfter the required uptake of hydrogen, the mixture is filtered
  2. washthe catalyst washed with fresh ethanol
  3. concentrationThe ethanol solution is then concentrated in vacuo
  4. customthe residue recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-b68a5fb89a654044a40c3a10d2f81774
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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