Methanol → 1-Oxo-2-{p-(carboxymethyl)-phenyl}-isoindoline

HRID 435167Notes

Reaction equation

HRID 435167 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][OH:13].B.[K].O>C(O)(=O)C>[O:13]=[C:12]1[C:6]2[C:5](=[CH:4][CH:3]=[CH:2][CH:7]=2)[CH2:8][N:1]1[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 145334-Aminophenylacetic acidHCID 24201897CID 24201897

Product 1

HCID 128542191-Oxo-2-{p-(carboxymethyl)-phenyl}-isoindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.64 g of o-phthalaldehydic acid methyl ester and 1.5 g of p-aminophenylacetic acid were added to 30 ml of methanol to form a mixture which was agitated at room temperature for one hour and incorporated with 0.54 g of potassium boron hydride in several portions. The whole was reacted at room temperature for 15 hours and freed from the solvent by distillation at a reduced pressure to obtain a residue. The thus obtained residue was incorporated with 50 ml of water and then with a small amount of acetic acid to form an acidic solution, after which crystals precipitated from said solution were filtered off, dried and recrystallized from ethanol thereby to obtain 2.4 g of 1-oxo-2-{p-(carboxymethyl)-phenyl}-isoindoline having the following properties:

Workup

  1. customto form a mixture which
  2. customThe whole was reacted at room temperature for 15 hours
  3. distillationfreed from the solvent by distillation at a reduced pressure
  4. customto obtain a residue
  5. customafter which crystals precipitated
  6. filtrationwere filtered off
  7. customdried
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-74063f74ac52448b9d4230492e073fbe
Source dataset
uspto-grants-1983_08
Patent number
US04400520

Reaction notes

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