4-(Phenylamino)benzoic acid → Methyl 4-anilinobenzoate

HRID 1108623Notes

Reaction equation

HRID 1108623 reaction equation
[C:1]1([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:18]O>>[C:1]1([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([O:14][CH3:18])=[O:13])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 2923314-(Phenylamino)benzoic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 614877Methyl 4-anilinobenzoate

Procedure

30 ml of 10% hydrogen chloride-methanol was added to 1.59 g (7.46 mmol) of 4-(phenylamino)benzoic acid and the mixture was refluxed overnight under heating. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed with a sodium hydrogencarbonate aqueous solution and brine, and dried (MgSO4). The solvent was distilled off and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1 (v/v)) to obtain 1.66 g (7.30 mmol) of methyl 4-(phenylamino)benzoate as a pale yellow solid. Its spectroscopic data are as follows:

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureunder heating
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with a sodium hydrogencarbonate aqueous solution and brine
  6. dry with materialdried (MgSO4)
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1 (v/v))

Sources & evidence

ORD record
ord-63b38e372e2f408d91d4a8f61e5d815d
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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