p-Toluenesulfonic acid → Methyl 3-amino-4-(1-pyrrolidinyl)benzoate

HRID 248672Notes

Reaction equation

HRID 248672 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:5]([OH:7])=[O:6].[C:16]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10762623-Amino-4-pyrrolidin-1-yl-benzoic acid

Product 1

HCID 15670372Methyl 3-amino-4-(1-pyrrolidinyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-4-(1-pyrrolidinyl)benzoic acid.hemioxalate (5.0 g) is suspended in methanol (40 ml) and thereto is added p-toluenesulfonic acid (2.5 g), and the mixture is refluxed for 3 hours. Mathanol is distilled off under reduced pressure, and the residue is extracted with ethyl acetate (100 ml). The extract is washed with 5% aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution in this order, dried over anhydrous sodium sulfate, and ethyl acetate is distilled off to give methyl 3-amino-4-(1-pyrrolidinyl)benzoate (3.4 g).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. distillationMathanol is distilled off under reduced pressure
  3. extractionthe residue is extracted with ethyl acetate (100 ml)
  4. washThe extract is washed with 5% aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution in this order
  5. dry with materialdried over anhydrous sodium sulfate, and ethyl acetate
  6. distillationis distilled off

Sources & evidence

ORD record
ord-1cb5122614494d5ebb02d86425299270
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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