Reacción #2348129

Ecuación de reacción

4-Hydroxybenzoic acid

aniline

EDCI

→

4-Hydroxy-N-phenyl-benzamide

Rendimiento 29.2%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente