Dimethylformamide → 2-(Nitrophenyl)amino-3,4-dimethylbenzoic acid

HRID 2270916Notes

Reaction equation

HRID 2270916 reaction equation
[CH3:1][C:2]1[C:3](I)=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[N+:13]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18])([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.[Cu]>[N+:13]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][C:3]1[C:2]([CH3:1])=[C:10]([CH3:11])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 69462-NitroanilineHCID 11430Potassium CarbonateHCID 111966352-Iodo-3,4-dimethylbenzoic acid

Product 1

HCID 227424482-(Nitrophenyl)amino-3,4-dimethylbenzoic acidYield 24.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

10 g of 3,4-dimethyl-2-iodobenzoic acid, 6 g of 2-nitroaniline, 250 mg of powdery copper and 25 g of potassium carbonate were added to N,N-dimethylformamide and heated under reflux while stirring for 2 hr. Then the reaction mixture was cooled to room temperature and diluted with water. After adjusting the pH value thereof to pH 4 with conc. hydrochloric acid, it was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give 2.5 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. extractionto pH 4 with conc. hydrochloric acid, it was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporating the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-744f7cb4938b47978c3b21305167dc15
Source dataset
uspto-grants-2001_12
Patent number
US06333322B1

Reaction notes

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