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

HRID 885090Notes

Reaction equation

HRID 885090 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.Cl>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 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

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 EDCl (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-99459ac997744331b1ac3c4a8874cf02
Source dataset
uspto-grants-2012_08
Patent number
US08242144B2

Reaction notes

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