2-Nitrophenyl phenyl ether → Benzenamine, 2-phenoxy-

HRID 1618802

Reaction equation

HRID 1618802 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[H][H]>CO.[Pd]>[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 166612-Nitrophenyl phenyl etherHCID 178418361HCID 178418361, compound

Product 1

HCID 75899Benzenamine, 2-phenoxy-Yield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Nitrodiphenyl ether (16 g, 74 mmol) in methanol (250 ml) was shaken with palladium on charcoal (1.6 g) under an atmosphere of hydrogen at 20-50° C. for 30 min. There was a rapid uptake of hydrogen and a detectable exotherm 20-50° C. with the temperature rapidly rising before cooling. Shaking was stopped for short periods to control the temperature from rising above 50° C. The reaction was then filtered through celite and concentrated in high vacuum to give 2-aminodiphenyl ether as an oil (13.5 g, 72.9 mmole, 98%) that crystallized on standing to give a buff solid.

Workup

  1. customa detectable exotherm 20-50° C.
  2. temperaturebefore cooling
  3. waitwas stopped for short periods
  4. customfrom rising above 50° C
  5. filtrationThe reaction was then filtered through celite
  6. concentrationconcentrated in high vacuum

Sources & evidence

ORD record
ord-328f0005a0db46f6ba8c45f44d2a743d
Source dataset
uspto-grants-2014_07
Patent number
US08771641B2

Linked notes

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