Water → N-(4-aminophenyl)-2-hydroxybenzamide

HRID 1268034Notes

Reaction equation

HRID 1268034 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:20])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)(=O)C.C(=O)(O)[O-].[Na+].O.[Cl-].[Na+]>CO>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:11](=[O:20])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[OH:4])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 18543278HCID 18543278, compound

Product 1

HCID 2781453N-(4-aminophenyl)-2-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-aminophenylcarbamoyl)phenyl acetate (580 mg) in methanol (10 mL) is added saturated sodium bicarbonate (2 mL) and water (3 mL). The mixture is heated at 80° C. for 30 minutes, then poured into half-saturated aqueous sodium chloride and extracted with ethyl acetate. The ethyl acetate solution is dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oil which is then triturated with diethyl ether to provide the desired product as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate solution is dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil which
  5. customis then triturated with diethyl ether

Sources & evidence

ORD record
ord-70ade6c842b4411ba45ac6c94bfbcf7b
Source dataset
uspto-grants-2003_04
Patent number
US06555561B2

Reaction notes

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