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

HRID 460513Notes

Reaction equation

HRID 460513 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
140 °C

Procedure

1.3 g of 3-fluoro-4-nitrophenol and 2.7 g of 4-methylaniline were mixed and stirred for 14 hours at 140° C. After cooling, it was dissolved in ethyl acetate and extracted three times with 4N aqueous hydrochloric acid. The organic phase was washed with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was crystallized from diisopropyl ether. 1.70 g was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with 4N aqueous hydrochloric acid
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customthe residue was crystallized from diisopropyl ether
  7. custom1.70 g was obtained

Sources & evidence

ORD record
ord-4351860afca546aab13ba478a372e22c
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Reaction notes

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