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

HRID 2296724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2296724
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 227424482-(Nitrophenyl)amino-3,4-dimethylbenzoic acidAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9dfe25a6a6524c208b04296e70d60afe
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489336B2

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