3-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)-1,1'-biphenyl → 4-(2-Chloro-4-phenylphenoxy)-2,5-dimethyl-3-chloroaniline

HRID 980566Notes

Reaction equation

HRID 980566 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N+:12]([O-])=O)=[C:7]([CH3:15])[C:6]=1[Cl:16]>[Pt].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([NH2:12])=[C:7]([CH3:15])[C:6]=1[Cl:16]

Participants

4

Reactant 1

HCID 137729283-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)-1,1'-biphenyl

Product 1

HCID 137729294-(2-Chloro-4-phenylphenoxy)-2,5-dimethyl-3-chloroanilineYield 84.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

A 500 milliliter rocking Parr hydrogenator was charged with a solution of 13.5 grams (0.035 moles) of 4-(2-chloro-4-phenylphenoxy)-2,5-dimethyl-3-chloro-nitrobenzene prepared in Part A and 135 milliliters of toluene. To this solution was added 1.0 gram of a catalyst of 5% platinum on carbon and the reactor was sealed. The reactor was purged twice with nitrogen and then twice with hydrogen. Hydrogen was then introduced to a pressure of 31 psi and this pressure was maintained until the hydrogen up-take ceased, i.e., about 1.5 hours. The material was removed from the rector, filtered and concentrated (toluene removed under vacuum) to give a viscous oil. Crystallization from a hexane-ethyl acetate mixture afforded 10.6 grams of a tan powder having a melting point of 117° C.-119° C. Elemental analysis of the tan powder indicated the following:

Workup

  1. customthe reactor was sealed
  2. customThe reactor was purged twice with nitrogen
  3. additionHydrogen was then introduced to a pressure of 31 psi
  4. temperaturethis pressure was maintained until the hydrogen
  5. customi.e., about 1.5 hours
  6. customThe material was removed from the rector
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custom(toluene removed under vacuum)
  10. customto give a viscous oil
  11. customCrystallization from a hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-12f685de1c194d8d9fa72f998a545968
Source dataset
uspto-grants-1987_01
Patent number
US04638088

Reaction notes

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