4-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene → 3,5-Dimethyl4-(3'-isopropyl-4'-methoxyphenoxy)-aniline

HRID 2256481Notes

Reaction equation

HRID 2256481 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:21]([O-])=O)[CH:5]=[C:6]([CH3:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1>[Pt].C(O)C>[CH3:20][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([CH3:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:18])[CH3:19])[CH:10]=1)[NH2:21]

Participants

4

Reactant 1

HCID 103136024-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Product 1

HCID 100167993,5-Dimethyl4-(3'-isopropyl-4'-methoxyphenoxy)-aniline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

3,5-Dimethyl-4-(3'-isopropyl-4'-methoxyphenoxy)nitrobenzene (480 mg) and 50 mg of 10% platinum on carbon in 100 ml ethanol are reduced on a Parr shaker. Catalyst is removed by filtration through Celite and the filtrate stripped. The residue is taken up in ether and acidified with gaseous hydrogen chloride. The ether solution is chilled, filtered to remove insolubles, and stripped to afford 3,5-dimethyl-4-(3'-isopropyl-4'-methoxyphenoxy)-aniline hiedrochloride, m.p. 95°-100°.

Workup

  1. customCatalyst is removed by filtration through Celite
  2. temperatureThe ether solution is chilled
  3. filtrationfiltered
  4. customto remove insolubles

Sources & evidence

ORD record
ord-7c2ab23343aa4745863b87cdacbbe6f9
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

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