p-Toluenesulfonic acid → HCID 12837909, compound

HRID 2286516Notes

Reaction equation

HRID 2286516 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([OH:14])=[O:13])[NH:3]1.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[NH:3]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 281699(3-Oxo-2,3-dihydro-1H-isoindol-1-yl)acetic acid

Product 1

HCID 12837909HCID 12837909, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,3-dihydro-3-oxo-2H-isoindole-1-acetic acid (described by F. M. Rowe et al., J. Chem. Soc., 1098 (1936) 130 g, 0.682 mol) in methanol (1300 ml) containing 6.5 g of p-toluenesulfonic acid was refluxed with stirring for 3.5 hr. Most of the methanol was evaporated and the residue was dissolved in chloroform. The solution was washed with 5% aqueous sodium bicarbonate and water, dried and evaporated. The residue (125 g) was crystallized from isopropanol to give methyl 1,3-dihydro-3-oxo-2H-isoindole-1-acetate, mp 136°-138° C.

Workup

  1. temperaturewas refluxed
  2. customMost of the methanol was evaporated
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe solution was washed with 5% aqueous sodium bicarbonate and water
  5. customdried
  6. customevaporated
  7. customThe residue (125 g) was crystallized from isopropanol

Sources & evidence

ORD record
ord-e64e246f663245818f0a86287d6f939c
Source dataset
uspto-grants-1981_05
Patent number
US04267189

Reaction notes

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