1-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)naphthalene → 3-Chloro-4-[(4-chloronaphthalen-1-yl)oxy]-2,5-dimethylaniline

HRID 846270Notes

Reaction equation

HRID 846270 reaction equation
[Cl:1][C:2]1[C:3]([CH3:24])=[C:4]([N+:21]([O-])=O)[CH:5]=[C:6]([CH3:20])[C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([Cl:19])=[CH:11][CH:10]=1.[H][H]>C1(C)C=CC=CC=1.[Pt]>[Cl:1][C:2]1[C:3]([CH3:24])=[C:4]([CH:5]=[C:6]([CH3:20])[C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([Cl:19])=[CH:11][CH:10]=1)[NH2:21]

Participants

5

Reactant 2

HCID 132459651-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)naphthaleneHCID 178418361HCID 178418361, compound3×

Product 1

HCID 132460063-Chloro-4-[(4-chloronaphthalen-1-yl)oxy]-2,5-dimethylanilineYield 91.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

Into a solution containing 13.8 grams (38.1 mmol) of 3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethyl-1-nitrobenzene prepared in Part A in 400 milliliters of toluene was added 2.0 grams of a 5% platinum on carbon catalyst. The resulting mixture was placed in a one liter rocking Parr hydrogenation vessel. Hydrogen was introduced into the vessel to a pressure of 120 psi. The hydrogen pressure was maintained between 100-120 psi until hydrogen uptake ceased. The contents of the reactor vessel were then removed and filtered. Removal of the solvents from the filtrate afforded 11.6 grams of 3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethylaniline as a white solid having a melting point of 118° C.-125° C.

Workup

  1. customThe contents of the reactor vessel were then removed
  2. filtrationfiltered
  3. customRemoval of the solvents from the filtrate

Sources & evidence

ORD record
ord-20361ca16cef4a03b181dc63525e233b
Source dataset
uspto-grants-1992_08
Patent number
US05135953

Reaction notes

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