Hydrazine hydrate (1:1) → 4-((3-(1,1-Dimethyl-ethyl)phenyl)oxy)-2,5-dimethylaniline

HRID 2121833Notes

Reaction equation

HRID 2121833 reaction equation
O.NN.[CH3:4][C:5]([C:8]1[CH:9]=[C:10]([O:14][C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([N+:22]([O-])=O)=[CH:17][C:16]=2[CH3:25])[CH:11]=[CH:12][CH:13]=1)([CH3:7])[CH3:6]>C(O)CC.[Pd]>[CH3:7][C:5]([C:8]1[CH:9]=[C:10]([O:14][C:15]2[C:16]([CH3:25])=[CH:17][C:18]([NH2:22])=[C:19]([CH3:21])[CH:20]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])[CH3:6]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 234343612-Nitro-5-(3-tert-butylphenoxy)-p-xylene

Product 1

HCID 155445904-((3-(1,1-Dimethyl-ethyl)phenyl)oxy)-2,5-dimethylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
90 °C

Procedure

Hydrazine hydrate (4.3 ml) is added dropwise to a mixture of 1-{[3-(1,1-dimethylethyl)phenyl]oxy}-2,5-dimethyl-4-nitrobenzene (8.65 g) and 5% palladium-on-charcoal (100 mg) in n-propanol (60 ml) heated to 90° C. The reaction mixture is maintained at 90° C. for 2 h and then filtered through Celite. Concentration gives the title compound.

Workup

  1. temperatureThe reaction mixture is maintained at 90° C. for 2 h
  2. filtrationfiltered through Celite
  3. concentrationConcentration

Sources & evidence

ORD record
ord-3f1a4d389994407d964c9b199ed8c624
Source dataset
uspto-grants-2004_02
Patent number
US06696487B2

Reaction notes

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