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

HRID 1070849Notes

Reaction equation

HRID 1070849 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-82f81e91197441858e18a797f6d085c7
Source dataset
uspto-grants-2005_06
Patent number
US06903126B2

Reaction notes

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