4-Iodoaniline → 2-[(4-Iodophenyl)amino]benzoic acid

HRID 488520Notes

Reaction equation

HRID 488520 reaction equation
[K+].Br[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O-:7])=[O:6].[I:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>COCCOCCOC.O>[I:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:3]2[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=2[C:5]([OH:7])=[O:6])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 108934-IodoanilineHCID 11430Potassium CarbonateHCID 19205467Potassium o-bromobenzoate

Product 1

HCID 125070482-[(4-Iodophenyl)amino]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

A mixture of o-bromobenzoic acid potassium salt (47.8 g, 0.2 mol), 4-iodoaniline (43.8 g, 0.2 mol), K2CO3 (13.8 g, 0.1 mol), and cupric acetate (2.87 g, 6%) in diglyme (100 mL) was heated to reflux for 30 minutes. The reaction mixture was diluted with H2O (1.0 L) and filtered. The filtrate was acidified with diluted AcOH. The resulting precipitate was collected by filtration, washed with H2O and dried in a vacuum at 50° C. for 16 hours. Recrystallization from EtOAc gave the desired product, a solid (29.7 g, 0.087 mol, 44%). mp 205-206° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. filtrationfiltered
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with H2O
  6. customdried in a vacuum at 50° C. for 16 hours
  7. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-2d5f85c9a6ac4500b7370a4a4359cee7
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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