4-Hydroxybenzoic Acid → 4-hydroxy-N-phenylbenzaMide

HRID 2260947Notes

Reaction equation

HRID 2260947 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN=C=NCCCN(C)C>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 5647164-hydroxy-N-phenylbenzaMideYield 29.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

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

Sources & evidence

ORD record
ord-109404c252df4d07889f21c5b087c808
Source dataset
uspto-grants-2010_12
Patent number
US07846915B2

Reaction notes

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