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

HRID 48188

Reaction equation

HRID 48188 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-25156da413f74e3fb251e988748786fe
Source dataset
uspto-grants-2004_03
Patent number
US06703388B2

Linked notes

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