p-Toluidine → 3-(4-Methylphenyl)amino-4-nitrophenol

HRID 2245321Notes

Reaction equation

HRID 2245321 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:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>C(OCC)(=O)C>[CH3:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 222822113-(4-Methylphenyl)amino-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

5.4 g of 3-fluoro-4-nitrophenol and 4.8 ml of 4-methylaniline 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-396b07580d134ac1b3435e6260388577
Source dataset
uspto-grants-2010_03
Patent number
US07683081B2

Reaction notes

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