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

HRID 435166Notes

Reaction equation

HRID 435166 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7](O)O[C:9](=[O:10])[C:4]2=[CH:3][CH:2]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1.CO.B.[K]>C(O)(=O)C.O>[O:10]=[C:9]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH2:7][N:12]1[C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 145334-Aminophenylacetic acidHCID 38042593-Hydroxyisobenzofuran-1(3H)-oneHCID 24201897CID 24201897

Product 1

HCID 128542191-Oxo-2-{p-(carboxymethyl)-phenyl}-isoindolineYield 94.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1.5 g of o-phthalaldehydic acid 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. Then, the whole was reacted at room temperature of 5 hours and then freed from the solvent under a reduced pressure. The resulting residue was incorporated with 50 ml of water and then with a small amount of acetic acid to obtain an acidic solution, after which crystals precipitated from the thus obtained solution were filtered off, dried and recrystallized from ethanol to obtain 2.5 g of 1-oxo-2 -{p-(carboxymethyl)-phenyl}-isoindoline.

Workup

  1. customto form a mixture which
  2. customThen, the whole was reacted at room temperature of 5 hours
  3. customafter which crystals precipitated from the thus obtained solution
  4. filtrationwere filtered off
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e9eccb2a445b4061b843d09713a279f2
Source dataset
uspto-grants-1983_08
Patent number
US04400520

Reaction notes

Loading…