Citric Acid → 2-(4-(4-Amino-2-nitrophenoxy)-2,3-dimethylphenyl)acetic acid

HRID 2423287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423287
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([CH3:12])[C:3]=1[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].F[C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.O>[NH2:25][C:24]1[CH:26]=[CH:27][C:21]([O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([CH3:12])[C:3]=2[CH3:13])=[C:22]([N+:28]([O-:30])=[O:29])[CH:23]=1

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 677684-Fluoro-3-nitroanilineHCID 598647702-(4-Hydroxy-2,3-dimethylphenyl)acetic acid

Produkt 1

HCID 598648252-(4-(4-Amino-2-nitrophenoxy)-2,3-dimethylphenyl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Under an N2 atmosphere, 2-(4-hydroxy-2,3-dimethylphenyl)acetic acid (0.780 g, 4.33 mmol) was dissolved in DMSO (29 mL). Cesium carbonate (3.53 g, 10.8 mmol) was added and the reaction was allowed to stir at room temperature for 5 min. 4-Fluoro-3-nitroaniline (0.678 g, 4.33 mmol) was added and the reaction was heated to 80° C. for 2.25 h. The reaction was allowed to cool to room temperature and diluted with water. Citric acid was added to pH 4 and the reaction was extracted with ethyl acetate. The layers were separated and the aqueous layer was washed with additional ethyl acetate. The organics were combined, dried (Na2SO4), filtered, and concentrated in vacuo. Flash column chromatography of the residue, eluting with 0% to 8% methanol in dichloromethane, afforded the title compound. LC-MS ESI (pos.) m/z: 317.2 (M+H).

Aufarbeitung

  1. temperaturethe reaction was heated to 80° C. for 2.25 h
  2. temperatureto cool to room temperature
  3. extractionthe reaction was extracted with ethyl acetate
  4. customThe layers were separated
  5. washthe aqueous layer was washed with additional ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washFlash column chromatography of the residue, eluting with 0% to 8% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-f366ac2c3cef43c8884261cff646ce87
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960567B2

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