3,5-Dimethylaniline → 3-(3,5-Dimethylphenyl)amino-4-nitrophenol

HRID 1393549Notes

Reaction equation

HRID 1393549 reaction equation
F[C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[NH2:16]>C(OCC)(=O)C>[CH3:12][C:13]1[CH:14]=[C:15]([NH:16][C:2]2[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])[CH:17]=[C:18]([CH3:20])[CH:19]=1

Participants

4

Reactant 2

HCID 79493,5-DimethylanilineHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 219381543-(3,5-Dimethylphenyl)amino-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

5.4 g of 3-fluoro-4-nitrophenol and 4.3 ml of 3,5-dimethylaniline were mixed and stirred for 6 hours at 120° C. After cooling, it was taken up in ethyl acetate and water and extracted three times with 1N aqueous hydrochloric acid. The combined aqueous phases were extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was crystallized.

Workup

  1. temperatureAfter cooling
  2. extractionwater and extracted three times with 1N aqueous hydrochloric acid
  3. extractionThe combined aqueous phases were extracted three times with ethyl acetate
  4. customThe combined organic phases were dried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customthe residue was crystallized

Sources & evidence

ORD record
ord-bcea5b27711246bcb25a415921eaedd6
Source dataset
uspto-grants-2008_03
Patent number
US07345075B2

Reaction notes

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