p-Toluenesulfonic acid → HCID 22401157, compound

HRID 260312Notes

Reaction equation

HRID 260312 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.[C:13]1(C)[CH:18]=CC(S(O)(=O)=O)=C[CH:14]=1>C(O)C=C>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH2:18][CH:13]=[CH2:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 27354063-(3-Aminophenyl)propionic acid

Product 1

HCID 22401157HCID 22401157, compound

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Procedure

3-(3-Aminophenyl)propionic acid (1 g, 6.06 mM) was dissolved in allyl alcohol (25 ml), and toluene-4-sulfonic acid (1.21 g, 6.36 mM) added. The mixture was heated to reflux, the distillate being passed through 3 Å molecular sieves, for 24 hours. After neutralisation of the mixture with triethylamine, the solvent was removed, the residue dissolved in ethyl acetate, and washed with water, aqueous NaHCO3, brine, and dried (MgSO4), to give title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customAfter neutralisation of the mixture with triethylamine, the solvent was removed
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with water, aqueous NaHCO3, brine
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-514a77deaaca43ad9f0c97ddffd721d3
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

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