3-Chloro-2-(2,4-dimethylphenoxy)-1,4-dimethyl-5-nitrobenzene → 3-Chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylaniline

HRID 2351467Notes

Reaction equation

HRID 2351467 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10]([Cl:11])=[C:9]([CH3:12])[C:8]([N+:13]([O-])=O)=[CH:7][C:6]=1[CH3:16]>C1(C)C=CC=CC=1.[Pt]>[CH3:1][C:2]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10]([Cl:11])=[C:9]([CH3:12])[C:8]([NH2:13])=[CH:7][C:6]=1[CH3:16]

Participants

4

Reactant 1

HCID 148206053-Chloro-2-(2,4-dimethylphenoxy)-1,4-dimethyl-5-nitrobenzene

Product 1

HCID 148206063-Chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylaniline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-(2,4-dimethylphenoxy)-3,6-dimethyl-5-chloronitrobenzene (25 g, 81.8 mmol) in toluene (250 ml) was added 5% platinum on carbon (1.0 g). The resulting mixture was subjected to hydrogenation at 20 psi. After 4.5 hours, the reaction mixture was filtered through celite and concentrated to given an oil (24.5 g). It turned to a pinkish solid after high vacuum drying; mp 86°~88° C.

Workup

  1. filtrationthe reaction mixture was filtered through celite and
  2. concentrationconcentrated
  3. customdrying

Sources & evidence

ORD record
ord-f9543c2a64eb4df995d53d9d27299052
Source dataset
uspto-grants-1989_10
Patent number
US04873264

Reaction notes

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