Reaktion #2348129

Reaktionsgleichung

4-Hydroxybenzoic acid

aniline

EDCI

→

4-Hydroxy-N-phenyl-benzamide

Ausbeute 29.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was then partitioned between EtOAc (200 mL) and water (200 mL)
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed consecutively with 1 N HCl, water, saturated sodium bicarbonate solution, water, and brine
4. 4
   Trocknendried over MgSO4
5. 5
   SonstigeSolvent was removed under reduced pressure
6. 6
   Sonstigethe crude product was purified by column chromatography

Vorschrift

4-Hydroxybenzoic acid (1.1 g, 7.96 mmoL) and aniline (742 mg, 7.23 mmol) were dissolved in 20 mL of dry DMF. To the above solution EDCI (1.53 g, 7.23 mmol) was added in one portion and the resulting mixture was stirred at rt overnight under nitrogen. The reaction mixture was then partitioned between EtOAc (200 mL) and water (200 mL). The organic layer was separated, washed consecutively with 1 N HCl, water, saturated sodium bicarbonate solution, water, and brine, and dried over MgSO4. Solvent was removed under reduced pressure and the crude product was purified by column chromatography using 10% EtOAc in hexane to give 450 mg (29% yield) of 4-Hydroxy-N-phenyl-benzamide. MS (ES) m/z: 214.08 (M+1).

Quelle