3-Methoxyaniline → (3-Methoxy-phenylamino)-phenyl-acetic acid

HRID 76998

Reaktionsgleichung

Reaktionsgleichung von HRID 76998
Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C1COCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:17][CH:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:5])=[O:4])[CH:18]=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 108243-MethoxyanilineHCID 97919Bromo(phenyl)acetic acid

Produkt 1

HCID 2759625(3-Methoxy-phenylamino)-phenyl-acetic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-2-phenylacetic acid (0.5 g, 2.28 mmol) and 3-methoxyaniline (0.54 mL, 4.56 mmol) in THF (12 mL) is refluxed for 4 hours. Solvent is removed under vacuum, the residue is taken up with 1M HCl and extracted with EtOAc. The organic phase is dried (Na2SO4), filtered and evaporated. The crude is purified by flash chromatography (DCM/MeOH=98/2 to 9/1) to obtain intermeaditae I116 as a white solid (0.58 g, 99% yield).

Aufarbeitung

  1. customSolvent is removed under vacuum
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude is purified by flash chromatography (DCM/MeOH=98/2 to 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-d2075340269f4f199e1ba8a3ca303395
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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