p-Toluenesulfonic acid → HCID 3095116, compound

HRID 1389503Notes

Reaction equation

HRID 1389503 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)=C[CH:16]=1>C(O)C>[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][CH2:15][CH3:16])=[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 3095116HCID 3095116, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,3-dihydro-3-oxo-1H-isoindole-1-acetic acid (described by F. M. Rowe et al., cited above, 2.0 g) in ethanol (40 ml) containing p-toluene-sulfonic acid (0.10 g) is refluxed with stirring for 4.0 hr. Most of the ethanol is evaporated and the residue is dissolved in chloroform. The solution is washed with water, dried and evaporated. The residue (2.2 g) is crystallized from benzenehexane to give ethyl 1,3-dihydro-3-oxo-2H-isoindole-1-acetate, mp 116°-118° C.

Workup

  1. temperatureis refluxed
  2. customMost of the ethanol is evaporated
  3. dissolutionthe residue is dissolved in chloroform
  4. washThe solution is washed with water
  5. customdried
  6. customevaporated
  7. customThe residue (2.2 g) is crystallized from benzenehexane

Sources & evidence

ORD record
ord-dd4bd2f017874720be4b5bd4f3b94f40
Source dataset
uspto-grants-1981_01
Patent number
US04244966

Reaction notes

Loading…