Reaction #2348129

Reaction equation

4-Hydroxybenzoic acid

aniline

EDCI

→

4-Hydroxy-N-phenyl-benzamide

Yield 29.2%

Solvents

DMF

Conditions

Workup

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

Procedure

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).

Source