p-Toluidine → Benzenamine, 4-methyl-N-(4-nitrophenyl)-

HRID 2297809Notes

Reaction equation

HRID 2297809 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[O-2].[Mg+2]>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 9590p-FluoronitrobenzeneHCID 6850729Magnesium monoxide

Product 1

HCID 94859Benzenamine, 4-methyl-N-(4-nitrophenyl)-Yield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
200 °C

Procedure

To a mixture of 4-nitro-fluorobenzene (250 mg, 1.77 mmol) and 4-amino-toluene (195 mL, 1.77 mmol) in 4 mL of water in a sealed tube was added magnesium oxide (86 mg, 2.126mmol). The suspension was stirred at 200° C. for 2 days. The reaction was cooled to ambient temperature and the suspension was diluted with water and filtered to remove insoluble material. The aqueous layer was extracted 3 times with ethyl acetate (50 mL) and the combined organic layers were washed with boronic acid (5%, 50 mL) and water, dried over magnesium sulfate and concentrated in vacuo to provide (4-nitro-phenyl)-p-tolyl-amine (190 mg, 47% yield). ). API MS: 229.20 (M+1).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. filtrationfiltered
  3. customto remove insoluble material
  4. extractionThe aqueous layer was extracted 3 times with ethyl acetate (50 mL)
  5. washthe combined organic layers were washed with boronic acid (5%, 50 mL) and water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44a4a380070e4b198870aed5c9890128
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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