Triethylamine → N-(4-iodophenyl)-2-nitroaniline

HRID 22491

Reaction equation

HRID 22491 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(OCC)(=O)C>[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108934-IodoanilineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 15045509N-(4-iodophenyl)-2-nitroanilineYield 48.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-fluoronitrobenzene (14 g, 100 mmol), 4-iodoaniline (11 g, 50 mmol) and triethylamine (14 ml, 100 mmol) was heated under reflux. After 48 h the reaction mixture was allowed to cool and ethyl acetate (300 ml) was added. The solution was washed with water (2×100 ml), aqueous 2M potassium hydroxide (100 ml) and brine (100 ml). The organics were dried over anhydrous magnesium sulphate and the solvent removed under reduced pressure to give an orange solid. Recrystalisation from ethyl acetate gave N-(4-iodophenyl)-2-nitroaniline (8.2 g, 48%) as an orange crystalline solid. deltaH (250 MHz, CDCl3) 9.39 (1H, s), 8.21 (1H, dd, J 8.5, 1.5 Hz), 7.71 (2H, dd, J 8.6, 2.0 Hz), 7.39 (1H, m), 7.24 (1H, m), 7.05 (2H, dd, J 8.6, 1.4 Hz), 6.83 (1H, m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. washThe solution was washed with water (2×100 ml), aqueous 2M potassium hydroxide (100 ml) and brine (100 ml)
  5. dry with materialThe organics were dried over anhydrous magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customto give an orange solid
  8. customRecrystalisation from ethyl acetate

Sources & evidence

ORD record
ord-01a5608ff8024c5eb682c47225811f55
Source dataset
uspto-grants-1995_06
Patent number
US05428168

Linked notes

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