Phthalic Anhydride → 7-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)heptanoic acid

HRID 261436Notes

Reaction equation

HRID 261436 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]>C(OCC)(=O)C>[C:4]1(=[O:6])[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]12

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 135807-Aminoheptanoic acid

Product 1

HCID 136226357-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)heptanoic acidYield 50.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of phthalic anhydride (5.3 g.) and 7-aminoheptanoic acid (5.8 g.) was heated at 185°-190° C. for 40 minutes and then cooled. The cooled partially solidified product was dissolved in ethyl acetate and the solution washed several times with dilute HCl. The organic layer was dried (MgSO4), filtered and evaporated to dryness and the residue recrystallized from acetic acid to give 7-phthalimidoheptanoic acid (5 g.), m.p. 112°-115° C.

Workup

  1. temperaturewas heated at 185°-190° C. for 40 minutes
  2. temperaturecooled
  3. temperatureThe cooled partially solidified product
  4. washthe solution washed several times with dilute HCl
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customthe residue recrystallized from acetic acid

Sources & evidence

ORD record
ord-845216acec664c98807af77566e6517d
Source dataset
uspto-grants-1979_08
Patent number
US04165377

Reaction notes

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