m-Toluidine → 3-Methyl-N-(4-nitrophenyl)benzenamine

HRID 2297807Notes

Reaction equation

HRID 2297807 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].[O-2].[Mg+2]>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:15][C:14]2[CH:13]=[C:12]([CH3:11])[CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 9590p-FluoronitrobenzeneHCID 6850729Magnesium monoxide

Product 1

HCID 275933-Methyl-N-(4-nitrophenyl)benzenamineYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
200 °C

Procedure

To a mixture of 4-nitro-fluorobenzene (250 mg, 1.77mmol) and 3-methyl aniline (190 mg, 1.77mmol) in 4 mL of water in a sealed tube was added magnesium oxide (86 mg, 2.126 mmol). 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)-m-tolyl-amine (190 mg, 47% yield). ). RP18-HPLC RT: 7.020 minutes; 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-14621820771d4a52aa5eff59995f2d0d
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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