Aniline → alpha-(Phenylamino)benzeneacetic acid

HRID 76963

Reaktionsgleichung

Reaktionsgleichung von HRID 76963
Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[C:6]1([CH:2]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]([OH:5])=[O:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 97919Bromo(phenyl)acetic acid

Produkt 1

HCID 19375alpha-(Phenylamino)benzeneacetic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

α-Bromophenylacetic acid (5.01 g, 23.2 mmol.) is dissolved in aniline (25 mL, 274 mmol) and the mixture reacted in a closed vessel under MW irradiation at 120° C. for 5 minutes (LC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 mL) is added to the reaction mixture and the resulting solid is filtered; 2M Na2CO3 (50 mL) is added to the solution, and the aqueous layer is washed with DCM (3×100 mL). The aqueous layer is acidified with 12N HCl (36 mL), and the title compound is recovered as racemic mixture by filtration (5.1 g, 97% yield, white solid).

Aufarbeitung

  1. customthe mixture reacted in a closed vessel under MW irradiation at 120° C. for 5 minutes (LC-MS monitoring: complete conversion)
  2. filtrationthe resulting solid is filtered
  3. addition2M Na2CO3 (50 mL) is added to the solution
  4. washthe aqueous layer is washed with DCM (3×100 mL)
  5. filtrationthe title compound is recovered as racemic mixture by filtration (5.1 g, 97% yield, white solid)

Quellen und Nachweise

ORD-Eintrag
ord-b9cecdcefa184330a95f0a0c4537d29a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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